Sodium borohydride → HCID 86657644, compound

HRID 217450Notes

Reaction equation

HRID 217450 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:29])([F:28])[C:5]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:6]=1[CH2:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[CH2:14][CH2:15][S:16]2)=[CH:11][CH:10]=1>CCO>[F:29][C:4]([F:3])([F:28])[C:5]1[CH:23]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:21]=[CH:20][C:6]=1[CH2:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]([OH:19])[CH2:14][CH2:15][S:16]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86657645HCID 86657645, compound

Product 1

HCID 86657644HCID 86657644, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of NaBH4 (93.1 mg) in EtOH (15 mL) was added dropwise a solution of 7-{[2,4-bis(trifluoromethyl)benzyl]oxy}-2,3-dihydro-4H-thiochromen-4-one (1.0 g) in EtOH (5 mL) at 0° C. The reaction mixture was warmed to 25° C., followed by stirring for 3 hours. The reaction liquid was concentrated under reduced pressure and to the residue were added DCM (20 mL) and then saturated aqueous NH4Cl (30 mL) at 0° C., followed by stirring for 1 hour and extracting with DCM three times (30 mL×3). The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 60:40) to obtain 7-{[2,4-bis(trifluoromethyl)benzyl]oxy}thiochroman-4-ol (845 mg) as a white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure and to the residue
  3. additionwere added DCM (20 mL)
  4. customat 0° C.
  5. stirringby stirring for 1 hour
  6. extractionextracting with DCM three times (30 mL×3)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 60:40)

Sources & evidence

ORD record
ord-4cadddb4ca72475c8f5f5efe8ffaccf0
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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