Sodium borohydride → 2-(1-trityl-1H-imidazol-2-yl)ethanol

HRID 886008Notes

Reaction equation

HRID 886008 reaction equation
[C:1]([N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25][CH:26]=[O:27])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C1COCC1.O>[C:1]([N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25][CH2:26][OH:27])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 509908112-[1-(triphenylmethyl)-1H-imidazol-2-yl]acetaldehyde

Product 1

HCID 221201462-(1-trityl-1H-imidazol-2-yl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Crude 2-(1-trityl-1H-imidazol-2-yl)acetaldehyde (2.025 g (5.75 mmol) was dissolved in MeOH/THF (1:1, 40 ml) and NaBH4 (0.435 g, 11.5 mmol) was added portionwise to the above mixture. The mixture was stirred for 18 hours, diluted with 100 ml of water and extracted with 2×DCM. The combined organic extracts were washed with water, brine, dried over Na2SO4 and concentrated in vacuum. Weight of the residue 1.915 g (94%). 1H NMR (500 MHz, CDCl3) δ 7.35-7.31 (m, 9H), 7.12 (dd, J=6.7, 2.7, 6H), 6.93 (d, J=1.0, 1H), 6.74 (d, J=1.0, 1H), 5.04 (br, 1H), 3.46 (t, J=5.4, 2H), 2.00 (t, J=5.4, 2H).

Workup

  1. extractionextracted with 2×DCM
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-0132cae15b4e40e2ad6f9581f5936a19
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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