Sodium borohydride → HCID 21904667, compound

HRID 1246617Notes

Reaction equation

HRID 1246617 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH3:15])[C:8]([S:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1)C=C.[BH4-].[Na+]>C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:12][O:11][C:9]1[CH:10]=[C:5]([OH:4])[CH:6]=[C:7]([CH3:15])[C:8]=1[S:13][CH3:14]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21904712HCID 21904712, compound

Product 1

HCID 21904667HCID 21904667, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

The allyl ether from stage (i) (850 mg, 3.8 mmol) was dissolved in THF (38 mL) and treated with palladium tetrakis(triphenylphosphine) (440 mg, 0.38 mmol) and sodium borohydride (719 mg, 19 mmol). The reaction mixture was then heated to 45° C. for 18 h. After cooling to room temperature most of the THF was evaporated and the residue was partitioned between 2M NaOH (25 mL) and diethyl ether (25 mL). The aqueous layer was separated and the organic layer was re-extracted with 2M NaOH (25 mL). The combined aqueous layers were neutralised to pH 7–8 with concentrated HCl and extracted with EtOAc (2×25 mL). The combined organic extracts were dried (MgSO4) and evaporated to an orange solid of the title phenol (530 mg, 76%); δH (CDCl3, 400 MHz) 2.20 (3H, s), 2.41 (3H, s), 3.83 (3H, s), 6.26 (1H, s), 6.29 (1H, s); MS m/z (ES−) 183 (M−H+).

Workup

  1. customwas evaporated
  2. customthe residue was partitioned between 2M NaOH (25 mL) and diethyl ether (25 mL)
  3. customThe aqueous layer was separated
  4. extractionthe organic layer was re-extracted with 2M NaOH (25 mL)
  5. extractionextracted with EtOAc (2×25 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customevaporated to an orange solid of the title phenol (530 mg, 76%)

Sources & evidence

ORD record
ord-00a85cafe24e4052a62d8bab5c5cabfa
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Reaction notes

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