Hydrochloric Acid → 4′-(1H-Indol-1-yl)[1,1′-biphenyl]-4-methanol

HRID 2113185Notes

Reaction equation

HRID 2113185 reaction equation
[BH4-].[Na+].[N:3]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.C1COCC1.Cl>O.C(O)C>[N:3]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 59655959HCID 59655959, compound

Product 1

HCID 596961964′-(1H-Indol-1-yl)[1,1′-biphenyl]-4-methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (783 mg, 20.6 mmol) was added portion-wise to a stirred solution of aldehyde (prepared in example 4) (3.06 g, 10.3 mmol) in a mixture of anhydrous THF and ethanol (1:1; 100 mL) at room temperature. The reaction mixture was stirred for 10 minutes at room temperature (TLC control), poured into water (50 mL) and acidified to pH 4 with 2N hydrochloric acid, and then extracted with diethyl ether (3×20 mL). The combined extract was washed with 0.5 N hydrochloric acid (2×10 mL), water and finally brine. The ethereal solution was dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 30% ethyl acetate/hexane as eluent, afforded the title compound has a white solid (2.80 g, 91%); 1H NMR (CDCl3, 300 MHz) δ 7.55-7.78 (7H, m, Ar-H), 7.52 (2H, d, J=8 Hz, Ar-H), 7.41 (1H, d, J=3.5 Hz, Ar-H), 7.22 (3H, m, Ar-H), 6.72 (1H, d, J=3.5 Hz, Ar-H), 4.79 (2H, d, J=5.5 Hz, CH2O).

Workup

  1. extractionextracted with diethyl ether (3×20 mL)
  2. extractionThe combined extract
  3. washwas washed with 0.5 N hydrochloric acid (2×10 mL), water and finally brine
  4. dry with materialThe ethereal solution was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the product by flash column chromatography

Sources & evidence

ORD record
ord-4a0ada8d8a3344c7ba6e96eba9d1ab2a
Source dataset
uspto-grants-2009_04
Patent number
US07524878B2

Reaction notes

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