Potassium tert-butoxide → (2R)-2-[(4-fluorophenoxy)methyl]oxirane

HRID 1723435Notes

Reaction equation

HRID 1723435 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C@@H:8]([OH:11])[CH2:9]O)=[CH:4][CH:3]=1.CC(C)(C)[O-].[K+]>O1CCCC1>[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C@H:8]2[CH2:9][O:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 53648274(+)-(S)-3-(4-fluorophenoxy)-1,2-propanediol

Product 1

HCID 6932897(2R)-2-[(4-fluorophenoxy)methyl]oxiraneYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 13.4 parts of (+)-(S)-3-(4-fluorophenoxy)-1,2-propanediol, O1 -4-methylbenzenesulfonate and 45 parts of tetrahydrofuran were added 4.9 parts of kalium 1,1-dimethyl ethoxide. The whole was stirred for 30 minutes at room temperature. It was filtered over Hyflo, washed with tetrahydrofuran and the filtrate was evaporated. The residue was distilled, yielding 3.8 parts (57.3%) of (-)-(R)-[(4-fluorophenoxy)methyl]oxirane; bp. 54° C. at 66.5 Pa; [α]D =4.08 (c=0.5% in trichloromethane) (148).

Workup

  1. filtrationIt was filtered over Hyflo
  2. washwashed with tetrahydrofuran
  3. customthe filtrate was evaporated
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-f0fe28e32d2f49028767ed15f4999564
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

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