Ethyl bromoacetate → 5-{3-(1-ethoxycarbonylmethoxy)-4-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-phenyl}-5-oxo-pentanoic acid methyl ester

HRID 1707300Notes

Reaction equation

HRID 1707300 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[C:11]([OH:30])[CH:10]=1)=[O:8].[CH2:32]([O:34][C:35](=[O:38])[CH2:36]Br)[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]/[C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[C:11]([O:30][CH2:36][C:35]([O:34][CH2:32][CH3:33])=[O:38])[CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 231781395-(3-hydroxy-4-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-phenyl}-5-oxopentanoic acid methyl ester

Product 1

HCID 231781345-{3-(1-ethoxycarbonylmethoxy)-4-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-phenyl}-5-oxo-pentanoic acid methyl esterYield 111.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under the conditions of example 1A, 420 mg of 5-(3-hydroxy-4-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-phenyl}-5-oxopentanoic acid methyl ester is reacted with 167 mg of bromoacetic acid ethyl ester in 4 ml of dimethylformamide in the presence of 650 mg of cesium carbonate and worked up. 562 mg of 5-{3-(1-ethoxycarbonylmethoxy)-4-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-phenyl}-5-oxo-pentanoic acid methyl ester is obtained as colorless oil.

Sources & evidence

ORD record
ord-5a54d7fbb95346fbb3c64debb2cb3537
Source dataset
uspto-grants-1994_10
Patent number
US05352701

Reaction notes

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