Tetramethylammonium hydroxide → HCID 70052379, compound

HRID 466236Notes

Reaction equation

HRID 466236 reaction equation
[P:1]([O-:18])([O:10]CC1C=CC=CC=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[CH3:20][N+:21]([CH3:24])([CH3:23])[CH3:22]>C(#N)C.O>[CH2:3]([O:2][P:1]([O-:18])[O-:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][N+:21]([CH3:24])([CH3:23])[CH3:22].[CH3:20][N+:21]([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 60966Tetramethylammonium hydroxideHCID 21904359Dibenzylphosphite

Product 1

HCID 70052379HCID 70052379, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Dibenzyl phosphite (29.4 g, 112 mmol) is dissolved in a mixture of acetonitrile (140 mL) and water (30 mL) and the reaction mixture is treated with 2.8M aqueous tetramethylammonium hydroxide (40 mL, 112 mmol) at room temperature for 24 hours. After being washed with ether (3×20 mL), the aqueous layer is concentrated in vacuo. The residue is dried under high vacuum at 70° for 12 hours to yield tetramethylammonium benzyl phosphite as a semi-solid. The latter compound (2 g, 8 mmol) and α-(phenylacetoxy)isobutyl bromide (prepared from phenylacetyl bromide and isobutyraldehyde according to Helv. Chim. Acta 61, 2047, 1978) (1.26 mL, 8 mmol) are stirred in acetone (15 mL) for 18 hours at room temperature. The precipitate is filtered through Celite. The filtrate is concentrated under reduced pressure and purified by flash-chromatography on silica gel eluting with 37.5% of ethyl acetate in hexane. Evaporation of the pure fractions gives the unsymmetrical (α-phenylacetyloxyisobutyl) benzyl phosphite as a colorless oil.

Workup

  1. washAfter being washed with ether (3×20 mL)
  2. concentrationthe aqueous layer is concentrated in vacuo
  3. customThe residue is dried under high vacuum at 70° for 12 hours

Sources & evidence

ORD record
ord-34a08bf3570e4819a05f95b4e9c02127
Source dataset
uspto-grants-1992_10
Patent number
US05155100

Reaction notes

Loading…