Methanol → HCID 57455338, compound

HRID 33103Notes

Reaction equation

HRID 33103 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][OH:6])#[N:2].C(N(CC)CC)C.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CO>ClCCl>[C:14]([O:6][CH2:5][CH2:4][CH2:3][C:1]#[N:2])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 2207054-hydroxybutanenitrile

Product 1

HCID 57455338HCID 57455338, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyano-1-n-propanol (16.85 g, 198 mmol, prepared by method of Blicke, et al., J. Org. Chem. 1961, 26, 3685) in dichloromethane (250 mL) were added triethylamine (80.1 g, 792 mmol) and trityl chloride (82.8 g, 297 mmol) at room temperature and the mixture was stirred for 16 h. To the reaction mixture was added methanol (25 mL) and stirred for 1 h. After concentration, the residue was purified on a column of silica gel using ethyl acetate and hexanes as eluent to give 40 g (61.7%) of the desired product.

Workup

  1. stirringstirred for 1 h
  2. concentrationAfter concentration
  3. customthe residue was purified on a column of silica gel

Sources & evidence

ORD record
ord-009a37cd18ae419ead4f70bea018eefc
Source dataset
uspto-grants-2008_09
Patent number
US07429571B2

Reaction notes

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