Sodium borohydride → HCID 59603165, compound

HRID 2061343Notes

Reaction equation

HRID 2061343 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:14][CH3:15])[C:6]2[O:10][C:9]([CH:11]=[O:12])=[CH:8][C:7]=2[CH:13]=1.[BH4-].[Na+]>C1COCC1.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:14][CH3:15])[C:6]2[O:10][C:9]([CH2:11][OH:12])=[CH:8][C:7]=2[CH:13]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59603182HCID 59603182, compound

Product 1

HCID 59603165HCID 59603165, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 4 (460 mg, 2.23 mmol) was dissolved in THF (5 mL) and EtOH (1 mL). NaBH4 (102 mg, 2.68 mmol) was added portionwise at 0° C., with vigorous stirring. The suspension was stirred at 0° C. for 15 min and then at room temperature for 1 h. Solvents were evaporated off in-vacuo. The crude residue was taken up in EtOAc and washed with water, brine and dried (MgSO4). The residue was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (1:1) to give 5 (388 mg, 82%) as an oil. m/z=209.08 (M+H). 1H NMR (500 MHz, CDCl3): δ: 6.62 (1H, s, H-3), 6.60 (1H, s, H-6), 6.46 (1H, s, H-4), 4.76 (2H, s, 2-CH2), 3.99 (3H, s, OMe), 3.85 (3H, s, OMe). 13C NMR (500 MHz, CDCl3): δ: 157.23 (C-5), 156.72 (C-1), 145.36 (C-7), 139.50 (C-1a), 129.38 (C-4a), 104.62 (C-3), 96.96 (C-6), 94.58 (C-4), 57.98 (2-CH2), 55.95 (OMe), 55.83 (OMe).

Workup

  1. waitat room temperature for 1 h
  2. customSolvents were evaporated off in-vacuo
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. custompurified by flash chromatography
  6. washeluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-1c1e132683a848f5863c8a8ab3366b7d
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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