PRODUCTION OF (E)-HYDROINDAN-4-ILYDEENETHANOL DERIVATIVE

Japanese Patent JP3563135

B2

PURPOSE: To industrially and advantageously obtain the subject compound useful as a synthetic intermediate of a vitamin D derivative under mild conditions in high yield and stereoselectivity by a specific method.
CONSTITUTION: This compound of formula IV (R10 is H or an acyl) is obtained by reacting a hydroindanon derivative of formula I (R1 is the formula C(CH3)R3 R4, or OR5 [R4 is H and R' is an alkyl, an alkenyl, etc., or R3 is OR8 (R8 is an alkyl, an alkynyl, etc.); R5 us R8]; R2 is H or OR6 (R6 is R8)} with a metal vinyl compound (e.g. vinylmagnesium chloride) to afford a 4-vinyl-4- oxyhydroindan derivative of formula II (X is H or a metal atom), acylating the resultant compound, preferably using a carboxylic acid anhydride, etc., as an acylating agent to give the compound of formula III and isomerizing the compound in the presence of a catalyst (preferably bisacetonitrile palladium chloride) and further, as necessary, deacylating the isomerized compound.

Takashi Takahashi
Nobu Nakazawa
Nao Nakagawa

JP32208194A

September 08, 2004

December 26, 1994

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KURARAY CO.,LTD.

C07D309/12; C07C29/128; C07C29/40; C07C29/56; C07C33/14; C07C35/23; C07C35/32; C07C43/23; C07C67/08; C07C67/34; C07C69/145; C07C69/16; C07F7/18; (IPC1-7): C07C29/128; C07C29/40; C07C33/14; C07C35/32; C07C67/08; C07C67/34; C07C69/145; C07D309/12; C07F7/18

JP6321830A
JP1110667A
JP6345689A
JP62234038A
JP55034781B1
JP55034780B1
JP47010371A

Journal of Organic Chemistry,1991年,Vol.56,No.1,pp461-3
Journal of Natural Products,1990年,Vol.53,No.3,pp565-72
Journal of the American Chemical Society,1983年,Vol.105,No.10,pp3270-3

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