Sodium borohydride → 5-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenol

HRID 1891436Notes

Reaction equation

HRID 1891436 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)=[O:16])=[C:11]([OH:31])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)[OH:16])=[C:11]([OH:31])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67497980(4-Benzyloxy-2-hydroxy-phenyl)-(4-benzyloxy-phenyl)-methanone

Product 1

HCID 674984815-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenol

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (4-benzyloxy-2-hydroxy-phenyl)-(4-benzyloxy-phenyl)-methanone (T1) (1.6 g, 4 mmol) in 40 mL of THF:MeOH (1:1) was added sodium borohydride (0.160 g, 4 mmol) and solution stirred at 40° C. for 4 hours. After complete consumption of starting material (TLC) the solvents were evaporated, till about 5 mL remaining in the flask. The residue was carefully neutralized with 1 N H2SO4, till pH dropped to 6 and yellow solution turned colorless. This was extracted with 50 mL (4×EtOAc:water, 1:1). The organic layers were combined and dried over sodium sulfate and evaporated to give (1.12 g, 68%) of T2 as pinkish white solid. 1H NMR (400 MHz, DMSO-d6) δ, 9.42(s, 1H, OH-Ph), 7.30(m, 13H, Ar—H2′/6′, 2×C6H5), 6.89 (d, 2H, Ar—H3′/5′), 6.44 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5), 6.38 (d, 1H, J=2.4 Hz, Ar—H3), 5.51 (d, 1H, CH—OH), 5.04 (s, 2H, PhCH2), 4.99 (s, 2H, PhCH2).

Workup

  1. customAfter complete consumption of starting material (TLC) the solvents
  2. customwere evaporated, till about 5 mL
  3. additiontill pH dropped to 6 and yellow solution
  4. extractionThis was extracted with 50 mL (4×EtOAc:water, 1:1)
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto give (1.12 g, 68%) of T2 as pinkish white solid

Sources & evidence

ORD record
ord-dcc1c6f6680f4ac9a29282e1fd47bea4
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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