Sodium borohydride → HCID 68651697, compound

HRID 646703Notes

Reaction equation

HRID 646703 reaction equation
[BH4-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11]2>CO.C(OCC)(=O)C>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH:13]([OH:17])[CH2:12][CH2:11]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11310424HCID 11310424, compound

Product 1

HCID 68651697HCID 68651697, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of sodium borohydride (0.22 g, 5.86 mmol) in methanol (6mL) at 0° C. was added a solution of 5-(2-thienyl)-2,3-dihydro-1H-inden-1-one (0.50 g, 2.34 mmol ) in methanol (2 mL). The reaction was slowly warmed to room temperature and stirred until the reaction was completed as monitored by thin layer chromatography (4 h). The reaction mixture was carefully quenched with 1.0 N aqueous hydrochloric acid at 0° C. until a clear solution was obtained. Diluted with ethyl acetate (200 mL), washed with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride (brine), and dried over anhydrous magnesium sulfate. Filtration, concentration and column chromatography on silica (7:3 hexanes/ethyl acetate) gave 5-(2-thienyl)-2,3-dihydro-1H-inden-1-ol (0.30 g, 59% yield) as solid. 1H NMR (400 MHz, CDCl3): 7.48 (m, 2H), 7.38 (br d, 1H), 7.26 (m, 2H), 7.08 (dd, 1H), 5.21 (t, 1H), 3.04 (m, 1H), 2.80 (m, 1H), 2.50 (m, 1H), 2.10 (brs, 1H), 1.93 (m, 1H).

Workup

  1. customas monitored by thin layer chromatography (4 h)
  2. customThe reaction mixture was carefully quenched with 1.0 N aqueous hydrochloric acid at 0° C. until a clear solution
  3. customwas obtained
  4. washwashed with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride (brine)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration, concentration and column chromatography on silica (7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-b52399567b0b4d379c8ec66c73078c61
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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