Methyl 5-bromo-2,2-dimethylpentanoate → rac-(E)-5-[2-(3-Methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]-2,2-dimethylpentanoic Acid Methyl Ester

HRID 1648069Notes

Reaction equation

HRID 1648069 reaction equation
[CH3:1][O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[C:11]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:10][CH:9]=[CH:8][C:7]=1[OH:25].Br[CH2:28][CH2:29][CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([O:34][CH3:35])=[O:33]>>[CH3:35][O:34][C:32](=[O:33])[C:31]([CH3:37])([CH3:36])[CH2:30][CH2:29][CH2:28][O:25][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[C:6]=1/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:26]

Participants

3

Reactant 2

HCID 13050502Methyl 5-bromo-2,2-dimethylpentanoateHCID 67694793rac-(E)-3-[2-hydroxy-6-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenyl]-2-propenoic acid methyl ester

Product 1

HCID 67780395rac-(E)-5-[2-(3-Methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]-2,2-dimethylpentanoic Acid Methyl EsterYield 92%

Procedure

Using the procedure of example 122, rac-(E)-3-[2-hydroxy-6-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenyl]-2-propenoic acid methyl ester (example 121) was alkylated with methyl 5-bromo-2,2-dimethylpentanoate giving the title compound, in 92% yield, as a colorless oil.

Sources & evidence

ORD record
ord-e6c7ec13122e439c97111cc39acd40cc
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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