Methanol → 3-(3-Chloro-benzo[b]thiophen-2-yl)-propan-1-ol

HRID 1814192Notes

Reaction equation

HRID 1814192 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[Cl:15].[Li+].[BH4-].CO.[OH-].[Na+]>CCOCC>[Cl:15][C:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[S:10][C:6]=1[CH2:5][CH2:4][CH2:3][OH:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 667607513-(3-Chloro-benzo[b]thiophen-2-yl)-propionic acid methyl ester

Product 1

HCID 219644313-(3-Chloro-benzo[b]thiophen-2-yl)-propan-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An ice cold solution of 3.63 g (14.3 mmol) of 15 in 60 mL of ether was treated with LiBH4 (621 mg, 28.5 mmol) and methanol (2 mL). After 30 min., 30 mL of 0.5 M NaOH solution was added. The mixture was extracted with ethyl acetate (2×25 mL) and the combined ethyl acetate solution washed with brine (50 mL), dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (5-20% ethyl acetate/hexane) to give 2.57 g (11.3 mmol, 79%) of the alcohol (16).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×25 mL)
  2. washthe combined ethyl acetate solution washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (5-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-01bef53bbfff4fc5a7a9494980c91c39
Source dataset
uspto-grants-2005_04
Patent number
US06875787B2

Reaction notes

Loading…