Tetrahydrofuran → HCID 70818320, compound

HRID 591071Notes

Reaction equation

HRID 591071 reaction equation
[Br:1][C:2]1[C:3]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:8])[S:5][C:6]=1[Cl:7].O1CCCC1.[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+]>C(O)C>[Br:1][C:2]1[C:3]([CH:9]([OH:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:8])[S:5][C:6]=1[Cl:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 70818481HCID 70818481, compoundHCID 131720822Sodium tetraborohydride

Product 1

HCID 70818320HCID 70818320, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of compound ethyl 2-(4-bromo-5-chloro-2-methylthiophen-3-yl)-2-oxoacetate (44b) (340 mg, 1.09 mmol), tetrahydrofuran (7 mL) and ethanol (1.7 mL) was added sodium tetraborohydride (37.2 mg, 0.98 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hours. The mixture was quenched with hydrochloric acid 1N and extracted with ethyl acetate twice. The organic extract was washed with brine twice, dried over sodium sulfate, filtered and concentrated in vacuo to afford the crude alcohol (44c) as a colorless oil (335 mg, 1.07 mmol, 98%).

Workup

  1. customThe mixture was quenched with hydrochloric acid 1N
  2. extractionextracted with ethyl acetate twice
  3. extractionThe organic extract
  4. washwas washed with brine twice
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-397d63dd3928496581b293d53ee8448d
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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