Sodium Carbonate Monohydrate → 3-(5-Bromothiophen-2-yl)-3-hydroxypropyl acetate

HRID 1484972Notes

Reaction equation

HRID 1484972 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]([C:9]1[S:10][C:11]([Br:14])=[CH:12][CH:13]=1)=[O:8])(=[O:3])[CH3:2].[BH4-].[Na+].C([O-])([O-])=O.[Na+].[Na+].O>C1COCC1>[C:1]([O:4][CH2:5][CH2:6][CH:7]([C:9]1[S:10][C:11]([Br:14])=[CH:12][CH:13]=1)[OH:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 2735133Sodium Carbonate MonohydrateHCID 4311764Sodium borohydrideHCID 581694203-(5-Bromothiophen-2-yl)-3-oxopropyl acetate

Product 1

HCID 581691293-(5-Bromothiophen-2-yl)-3-hydroxypropyl acetateYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(5-bromothiophen-2-yl)-3-oxopropyl acetate (2.4 g, 8.8 mmol, 1 eq) in THF (150 ml) was stirred at 0° C., and NaBH4 (401.2 mg, 10.6 mmol, 2 eq) was added slowly and the reaction was stirred at 23° C. After 1 hour, Na2CO3.H2O was added. After 30 min the mixture was filtered and extracted with EtOAc (3×50 ml). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated to give a residue. The residue was purified by silica gel column chromatography (PE/EtOAc=5:1 as eluant) to give 3-(5-bromothiophen-2-yl)-3-hydroxypropyl acetate (1.92 g, 78.2%) as white solid. LC-MS (m/z)=279.1 [M+H]+

Workup

  1. stirringthe reaction was stirred at 23° C
  2. filtrationAfter 30 min the mixture was filtered
  3. extractionextracted with EtOAc (3×50 ml)
  4. washThe combined organic phases were washed (brine)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue
  9. customThe residue was purified by silica gel column chromatography (PE/EtOAc=5:1 as eluant)

Sources & evidence

ORD record
ord-5f2bb86f34eb4a41920f7b779436d858
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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