Ethyl 4-(benzyloxy)-3-oxobutanoate → Ethyl 4-benzyloxy-2-[2-(3-cyclopentoxy-4-methoxyphenyl)-2-oxoethyl]-3-oxobutyrate

HRID 2097534Notes

Reaction equation

HRID 2097534 reaction equation
[CH2:1]([O:8][CH2:9][C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:23]=1)=[O:21].BrCC(C1C=CC(OC(F)F)=C(OCC2CC2)C=1)=O>>[CH2:1]([O:8][CH2:9][C:10](=[O:17])[CH:11]([CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:23]=1)=[O:21])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 9813448Ethyl 4-(benzyloxy)-3-oxobutanoateHCID 544385052-Bromo-1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethan-1-oneHCID 866270522-Bromo-1-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)ethanone

Product 1

HCID 66602831Ethyl 4-benzyloxy-2-[2-(3-cyclopentoxy-4-methoxyphenyl)-2-oxoethyl]-3-oxobutyrateYield 75%

Procedure

Reaction and post treatment were carried out in the same manner as in Reference example 45-(b) except for using 7.65 g (32.4 mmol) of ethyl 4-benzyloxy-3-oxobutyrate in place of ethyl 4-(4-methoxybenzyloxy)-3-oxobutyrate, and using 8.45 g (27 mmol) of 2-bromo-1-(3-cyclopentoxy-4-methoxyphenyl)ethanone obtained in Reference example 47-(a) in place of 2-bromo-1-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)ethanone, respectively, whereby 9.49 g of the title compound was obtained as a yellowish oil. (Yield: 75%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-fe035c19436945dfa90e5ee4a7b933ed
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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