Sodium borohydride → HCID 86659567, compound

HRID 1431026Notes

Reaction equation

HRID 1431026 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([O:10][CH:11]([CH3:13])[CH3:12])[CH:7]=[C:6]([C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([P:21]([O:27][CH:28]([CH3:30])[CH3:29])([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH:5]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([O:10][CH:11]([CH3:12])[CH3:13])[CH:7]=[C:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([P:21]([O:23][CH:24]([CH3:26])[CH3:25])([O:27][CH:28]([CH3:29])[CH3:30])=[O:22])=[CH:17][CH:16]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86659568HCID 86659568, compound

Product 1

HCID 86659567HCID 86659567, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[4-(diisopropoxy-phosphoryl)-benzoyl]-5-isopropoxy-benzoic acid methyl ester (750 mg, 1.62 mmol) in MeOH (30 mL) was added NaBH4 (120 mg, 3.17 mmol) at rt. Stirred at rt overnight. On the second day, the mixture was concentrated. The residue was partitioned between EOAc/HCl (0.1 M) and the organic layer was separated, washed with brine, dried, and concentrated. The resulting residue was dissolved in a mixture of EOAc/EtOH (20 mL, v/v=10:1) and hydrogenated over Pd/C (10%, 200 mg) using a Parr apparatus overnight. Then the mixture was filtered through a Celite plug. The filtrate was concentrated, azeotroped with CH2Cl2 to give the title compound (720 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 7.72 (dd, J=13.8 Hz, 2H), 7.45 (m, 1H), 7.40 (m, 1H), 7.25 (dd, J=8, 4 Hz, 2H), 6.87 (m, 1H), 4.62-4.70 (m, 2H), 4.53-4.61 (m, 1H), 3.88 (s, 3H), 1.36 (d J=6 Hz, 6H), 1.32 (d J=6 Hz, 6H), 1.22 (d, J=6 Hz, 12H).

Workup

  1. concentrationOn the second day, the mixture was concentrated
  2. customThe residue was partitioned between EOAc/HCl (0.1 M)
  3. customthe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe resulting residue was dissolved in a mixture of EOAc/EtOH (20 mL, v/v=10:1)
  8. customa Parr apparatus overnight
  9. filtrationThen the mixture was filtered through a Celite plug
  10. concentrationThe filtrate was concentrated
  11. customazeotroped with CH2Cl2

Sources & evidence

ORD record
ord-7e8b4b4d06dc4cde937901d794476086
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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