2,2,2-Trifluoroethanol → HCID 19381016, compound

HRID 258319Notes

Reaction equation

HRID 258319 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Br[CH2:10][C:11]([O:13][CH3:14])=[O:12]>O1CCCC1>[F:3][C:4]([F:8])([F:7])[CH2:5][O:6][CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 19381016HCID 19381016, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of sodium hydride (1.648 g, 68.66 mmol) in tetrahydrofuran (220 mL) at 0° C. was added 2,2,2-trifluoroethanol (5.0 mL, 68.66 mmol). After 5 minutes, the reaction was allowed to warm to room temperature and methyl 2-bromoacetate (6.2 mL, 65.39 mmol) was added. After stirring for 72 hours, the mixture was filtered through diatomaceous earth with ether washes. The filtrate was concentrated and distilled to afford the title compound as a colorless oil (8.26 g, 73%), bp 155°-60° C., MS(CI): 173(M+H); H-NMR (300 MHz, DMSO-d6): 3.68(s, 3H), 4.16(q, J=9.2 Hz, 2H), 4.33(s, 2H).

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth with ether washes
  2. concentrationThe filtrate was concentrated
  3. distillationdistilled

Sources & evidence

ORD record
ord-1b4e6061c4db43b484a943601731d4b0
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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