Propargyl alcohol → [3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester

HRID 1250111Notes

Reaction equation

[CH2:1]([OH:4])[C:2]#[CH:3].[C:5]([O:9][C:10](=[O:20])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=1)([CH3:8])([CH3:7])[CH3:6].[Cl-].[NH4+]>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:5]([O:9][C:10](=[O:20])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:3]#[C:2][CH2:1][OH:4])[CH:14]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

Conditions

Temperature: 77.5 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.66 g, 0.57 mmol) and propargyl alcohol (1.34 mL, 22.97 mmol) were added to a solution of (3-bromophenoxy) acetic acid tert-butyl ester (3.3 g, 11.49 mmol) in pyrrolidine (35 mL) under an argon atmosphere at room temperature. The mixture was heated at 75-80° C. for 2.5 hours. Excess saturated ammonium chloride was added and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave [3-(3-hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester as a pale yellow oil (1.93 g, 64%).

Workup

extractionthe mixture was extracted with diethyl ether
washThe extract was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness
customPurification by flash chromatography
washeluting with hexane/ethyl acetate

Sources & evidence

ORD record: ord-00bf84f5715d49e0afb0ce73e180434c
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06335459B1

Reaction notes

Loading…