Sodium borohydride → HCID 23292349, compound

HRID 2061347Notes

Reaction equation

HRID 2061347 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]=[O:11])=[CH:7][C:6]=2[CH:12]=1.[BH4-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[CH:7][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10844747HCID 10844747, compound

Product 1

HCID 23292349HCID 23292349, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Compound 13 (180 mg, 1.10 mmol) was dissolved in EtOH (12 mL). NaBH4 (45 mg, 1.21 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 1.5 h. Solvents were evaporated off in-vacuo. The crude residue was taken up in EtOAc and washed with water, brine and dried (MgSO4). The solvent was evaporated off in vacuo. The residue was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (3:1) to give 14 (150 mg, 91%) as a white solid. 1H NMR (500 MHz, CDCl3): δ: 7.36 (1H, d, J=8.35 Hz, H-7), 7.19 (1H, d, J=7.80, H-4), 7.00 (1H, t, J=8.75H-6), 6.60 (1H, s, H-3), 4.75 (2H, s, CH2).

Workup

  1. waitat room temperature for 1.5 h
  2. customSolvents were evaporated off in-vacuo
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated off in vacuo
  6. custompurified by flash chromatography
  7. washeluting with hexane/EtOAc (3:1)

Sources & evidence

ORD record
ord-20e9c5a3c1ff49b888b019b6e0a7a4e4
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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