Ethyl 2-(diethoxyphosphoryl)butanoate → Ethyl 5,9-dimethyl-2-ethyl-11-(2,6,6-trimethyl-1cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate

HRID 2309203Notes

Reaction equation

HRID 2309203 reaction equation
[CH3:1][CH2:2][CH:3](P(OCC)(OCC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20]([CH3:25])([CH3:24])[C:19]=1/[CH:26]=[CH:27]/[C:28](/[CH3:37])=[CH:29]/[CH:30]=[CH:31]/[C:32](/[CH3:36])=[CH:33]/[CH:34]=O>>[CH3:36][C:32]([CH:31]=[CH:30][CH:29]=[C:28]([CH3:37])[CH:27]=[CH:26][C:19]1[C:20]([CH3:25])([CH3:24])[CH2:21][CH2:22][CH2:23][C:18]=1[CH3:17])=[CH:33][CH:34]=[C:3]([CH2:2][CH3:1])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 638015Retinal

Product 1

HCID 54016105Ethyl 5,9-dimethyl-2-ethyl-11-(2,6,6-trimethyl-1cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate

Procedure

In analogy to the procedure given in Example 1: Triethyl 2-phosphonobutyrate was reacted with retinal to give ethyl 5,9-dimethyl-2-ethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate, which was converted by the procedure of Example 2 to 5,9-dimethyl-2-ethyl-11(2,6,6-trimethyl -1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoic acid, m.p.=164°-165° C.

Sources & evidence

ORD record
ord-8e42cb2bb4be424f9dcf733296cfc43c
Source dataset
uspto-grants-1987_09
Patent number
US04694023

Reaction notes

Loading…