Sodium borohydride → HCID 21904669, compound

HRID 1246616Notes

Reaction equation

HRID 1246616 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([CH3:15])[C:8]2[S:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=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]>[CH3:15][C:13]1[C:8]2[S:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=[C:5]([OH:4])[CH:14]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21904696HCID 21904696, compound

Product 1

HCID 21904669HCID 21904669, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

The allyl ether from stage (i) (1.40 g, 6.3 mmol) was dissolved in THF (63 mL) and treated with sodium borohydride (1.19 g, 31.5 mmol) followed by palladium tetrakis(triphenylphosphine) (730 mg, 0.63 mmol), and the mixture was heated to 40° C. overnight. After cooling to room temperature 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 re-extracted with 2M NaOH (25 mL). The combined aqueous layers were acidified with concentrated hydrochloric acid to pH 7–8 and extracted with EtOAc (2×25 mL). The combined organic extracts were dried (MgSO4) and evaporated to a brown oil (10.73 g, 93%) of the desired title phenol; δH (CDCl3, 400 MHz) 2.17 (3H, s), 3.07 (2H, m), 4.33 (2H, m), 6.20 (1H, s), 6.31 (1H, s); MS m/z (TS+) 183 (MH+).

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 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 a brown oil (10.73 g, 93%) of the desired title phenol

Sources & evidence

ORD record
ord-34eed599b7694a3382f0f4517fb98002
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Reaction notes

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