Glycolaldehyde → HCID 53969551, compound

HRID 1019035Notes

Reaction equation

HRID 1019035 reaction equation
[Br-].[F:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][CH2:8][C:9]2[CH:34]=[CH:33][C:12]([CH2:13][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=C[C:10]=2[C:35](OC)=O)=[CH:5][CH:4]=1.[CH:41](=[O:44])CO.[C:45](=O)([O-])[O-:46].[K+].[K+].C1OCCOCCOCCOCCOCC[O:53]C1>ClCCl.O>[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[CH:8]=[C:9]([CH:10]=[CH:35][CH2:41][OH:44])[CH:34]=[CH:33][C:12]=2[C:13]([O:46][CH3:45])=[O:53])=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 756GlycolaldehydeHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 865903414-(4-Fluorophenethyl)-3-methoxycarbonylbenzyl triphenylphosphonium bromide

Product 1

HCID 53969551HCID 53969551, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-fluorophenethyl)-3-methoxycarbonylbenzyl triphenylphosphonium bromide (27 g, 46 mmol), glycolaldehyde (7.2 g; 92 mmol), potassium carbonate (13 g; 92 mmol) and 18-crown-6 (0.2 g) in dichloromethane (300 ml) was stirred for 2 days at ambient temperature under argon atmosphere. After addition of distilled water and extraction, the solution was evaporated to dryness to give methyl 2-(4-fluorophenyl)-4-(3-hydroxyprop-1-en-1-yl)benzoate which was used in the next step without further purification.

Workup

  1. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-ed5e4dde1807420b962ee6136595ecbc
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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