Water → HCID 14538205, compound

HRID 2108271Notes

Reaction equation

HRID 2108271 reaction equation
[H-].[Na+].[O:3]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][SH:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:18][C:19]([F:33])([F:32])[C:20]1([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=2)[O:22][CH2:21]1.O>CN(C)C=O.C(O)(=O)C>[O:3]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][S:14][CH2:21][C:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=1)([OH:22])[C:19]([F:18])([F:32])[F:33])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 13880753HCID 13880753, compoundHCID 14350403(3-Phenoxyphenyl)methanethiol

Product 1

HCID 14538205HCID 14538205, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.1 g) in N,N-dimethylformamide (10 cm3) at 0° C. was added 3-phenoxybenzyl thiol (0.28 g). After stirring for 30 minutes, 1,1,1-trifluoro-2-(4-ethoxyphenyl)-prop-2-ene oxide (0.3 g) was added. The reaction mixture was stirred for ten minutes before being added to water (25 cm3) and neutralised with acetic acid. The product was extracted into diethyl ether (200 cm3). The organic layer was dried over anhydrous sodium sulphate and the solvent removed by evaporation under reduced pressure. The resulting oil was purified by chromatography to give 1,1,1-trifluoro-2-(4-ethoxyphenyl)-2-hydroxyprop-3-yl 3-phenoxybenzyl sulphide as a colourless oil (0.4 g).

Workup

  1. stirringThe reaction mixture was stirred for ten minutes
  2. extractionThe product was extracted into diethyl ether (200 cm3)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. customthe solvent removed by evaporation under reduced pressure
  5. customThe resulting oil was purified by chromatography

Sources & evidence

ORD record
ord-61aa7c644fa3484d86c8e2535d00bb7f
Source dataset
uspto-grants-1990_06
Patent number
US04937388

Reaction notes

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