Trifluoroacetic acid → HCID 15550520, compound

HRID 1106461Notes

Reaction equation

HRID 1106461 reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]([CH:13]([C:15]2[O:19][C:18]([CH3:20])=[C:17]([CH3:21])[CH:16]=2)O)=[CH:11][C:10]2[CH:22]=[CH:23][CH:24]=[CH:25][C:9]1=2.[BH4-].[Na+]>C(=S)=S>[S:8]1[C:12]([CH2:13][C:15]2[O:19][C:18]([CH3:20])=[C:17]([CH3:21])[CH:16]=2)=[CH:11][C:10]2[CH:22]=[CH:23][CH:24]=[CH:25][C:9]1=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 15550519HCID 15550519, compound

Product 1

HCID 15550520HCID 15550520, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Trifluoroacetic acid (30 mL) was added dropwise to a rt, stirred suspension of benzo[b]thiophen-2-yl-(2,3-dimethyl-furan-5-yl)-methanol (9.56 g, 40.0 mmol) and sodium borohydride (7.0 g, 200 mL) in carbon disulfide (100 mL) under a try N2 atmosphere over a period of 30 min. After an additional 3 hours, the reaction mixture was carefully quenched and further diluted with aqueous ammonium chloride (250 mL). Aqueous mixture was extracted with ethyl ether (500 mL). The ethyl ether extract was washed with water and brine. Silica gel (100 mL) was added. Solvents were removed and the silica adsorbate was flash chromatographed (eluent 99:1 petroleum ether: ethyl acetate) to provide the title compound as an oil (3.75 g, 42%): NMR (CDCl3); δ7.74 (d, J=8 Hz, 1H), 7.67 (d, J=8, Hz, 1H), 7.35-7.22 (m, 2H), 7.08 (d, J=1 Hz, 1H), 5.93 (s, 1H), 4.15 (s, 2H), 2.17 (s, 3H), 1.90 (s, 3H); MS (EI): [M+], 242.

Workup

  1. customthe reaction mixture was carefully quenched
  2. additionfurther diluted with aqueous ammonium chloride (250 mL)
  3. extractionAqueous mixture was extracted with ethyl ether (500 mL)
  4. extractionThe ethyl ether extract
  5. washwas washed with water and brine
  6. additionSilica gel (100 mL) was added
  7. customSolvents were removed
  8. customchromatographed (eluent 99:1 petroleum ether: ethyl acetate)

Sources & evidence

ORD record
ord-7777839749b447929d9cf301fbea4d03
Source dataset
uspto-grants-2000_05
Patent number
US06057316

Reaction notes

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