Water → 2-(2-Chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol

HRID 1871508Notes

Reaction equation

HRID 1871508 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([C:8]1[C:16]([F:17])=[CH:15][C:11]2[S:12][CH:13]=[CH:14][C:10]=2[CH:9]=1)=[O:7].C1(C2(C3C=CC=CC=3)OB(C)N3CCC[C@H]23)C=CC=CC=1.B.O>O1CCCC1.C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([C:8]1[C:16]([F:17])=[CH:15][C:11]2[S:12][CH:13]=[CH:14][C:10]=2[CH:9]=1)[OH:7]

Participants

7

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 186916002-(2-Chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanone

Product 1

HCID 154085802-(2-Chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanolYield 99.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.5 g of 2-(2-chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanone in 45 ml of tetrahydrofuran is added 0.46 g of (R)-5,5-diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine at -10° C., and thereafter, 9.9 ml of 1 M borane solution of tetrahydrofuran is dropwise added thereto. The temperature of the resulting mixture is elevated to room temperature, and the mixture is stirred at the same temperature for 1.5 hours, after which 100 ml of water and 100 ml of ethyl acetate are added thereto. The resulting organic layer is separated, washed successively with water and a saturated saline solution and then dried over anhydrous magnesium sulfate. The solvent is then removed from the thus dried layer by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluent: toluene:ethyl acetate=10:1], to obtain 4.5 g of oily (+)-2-(2-chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol.

Workup

  1. customis elevated to room temperature
  2. customThe resulting organic layer is separated
  3. washwashed successively with water
  4. dry with materiala saturated saline solution and then dried over anhydrous magnesium sulfate
  5. customThe solvent is then removed from the thus dried layer by distillation under reduced pressure
  6. customThe residue obtained
  7. customis purified by a column chromatography [eluent: toluene:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-6fdf021fc5614454a047f99b5876d559
Source dataset
uspto-grants-2000_08
Patent number
US06103754

Reaction notes

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