Cesium carbonate → methyl(2S)-2-[4-fluoro-3-(3-hydroxypropyl)phenoxy]propanoate

HRID 2389323

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][OH:12].Cl[C@H:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C@@H:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][OH:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 4-fluoro-3-(3-hydroxypropyl)phenol (1.5 g), methyl (2R)-2-chloropropanoate (1.30 g) in DMSO (7.5 mL) was added Cs2CO3 (3.45 g) at ambient temperature. The mixture was stirred at 60° C. for 3 hours. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc (50 mL) and washed successively with water (30 mL) two times and brine (30 mL). The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=4:1-2:1) to give methyl(2S)-2-[4-fluoro-3-(3-hydroxypropyl)phenoxy]propanoate (1.51 g) as a colorless oil.

Workup

temperatureAfter cooling to ambient temperature
washwashed successively with water (30 mL) two times and brine (30 mL)
dry with materialThe organic layer was dried over anhydrous MgSO4
filtrationfiltered
customevaporated in vacuo
customto give crude oil
customThe crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=4:1-2:1)

Sources & evidence

ORD record: ord-6c2c0f1bedca4ae4af36eb8e4e219608
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273745B2

Linked notes

Loading…