4-Fluorophenol → HCID 18625833, compound

HRID 1268962Notes

Reaction equation

HRID 1268962 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH:28]([OH:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F:35][C:36]1[CH:41]=[CH:40][C:39](O)=[CH:38][CH:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH:28]([O:34][C:39]2[CH:40]=[CH:41][C:36]([F:35])=[CH:37][CH:38]=2)[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

Product 1

HCID 18625833HCID 18625833, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of diethyl azodicarboxylate (40% toluene solution, 6.40 ml) in toluene (3.0 ml) was added dropwise at room temperature to a solution of ethyl 3-(4-benzyloxyphenyl)lactate (10.0 g) obtained from Reference example 24(a), 4-fluorophenol (4.15 g) and triphenylphosphine (10.6 g) in toluene (10 ml). The reaction mixture was stirred for 2 hours at room temperature and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluant; dichloromethane/ethyl acetate=3/2) to afford the target compound (7.00 g) as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography on a silica gel column (eluant; dichloromethane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-d783dfdaeb1f42f1bcf51664dcd92942
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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