Diethyl 2-acetyl-2-[3-(1-acetoxycyclohexyl)-2-propyn-1-yl]azelate → 8-Acetyl-11-(1-hydroxycyclohexyl)undec-10-ynoic acid

HRID 372903Notes

Reaction equation

HRID 372903 reaction equation
[C:1]([C:4]([CH2:21][C:22]#[C:23][C:24]1([O:30]C(=O)C)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])C(OCC)=O)(=[O:3])[CH3:2].C(C(CC#CC(OC(=O)C)CCCCC)(CCCCCCC(OCC)=O)C(OCC)=O)(=O)C>>[C:1]([CH:4]([CH2:21][C:22]#[C:23][C:24]1([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 20322246Diethyl 2-acetyl-2-[3-(1-acetoxycyclohexyl)-2-propyn-1-yl]azelateHCID 20322248Diethyl 2-acetyl-2-(4-acetoxy-2-nonyn-1-yl)azelate

Product 1

HCID 203222738-Acetyl-11-(1-hydroxycyclohexyl)undec-10-ynoic acid

Procedure

This compound is prepared by the same procedure described in Example 35, Step B, except that diethyl 2-acetyl-2-[3-(1-acetoxycyclohexyl)-2-propyn-1-yl]azelate is substituted for diethyl 2-acetyl-2-(4-acetoxy-2-nonyn-1-yl)azelate. The chromatographically purified product is a yellowish viscous oil; pmr (CDCl3)δ 2.14 (3H,s CH3C0), 6.50 (2H,s OH and COOH).

Workup

  1. customThis compound is prepared by the same procedure

Sources & evidence

ORD record
ord-536f16e136324bcab0717ee5562c5830
Source dataset
uspto-grants-1978_05
Patent number
US04092356

Reaction notes

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