Dichloromethane → 6-(Dimethoxythiophosphoryl)hexanoic acid tert-butyl ester

HRID 496325Notes

Reaction equation

HRID 496325 reaction equation
C[S:2][P:3]([O-:6])[O:4][CH3:5].[C:7]([O:11][C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br)([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+].Cl[CH2:23]Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[C:7]([O:11][C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][P:3]([O:6][CH3:23])([O:4][CH3:5])=[S:2])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 11550568Tert-butyl 6-bromohexanoateHCID 86596782Dimethyl thiophosphite

Product 1

HCID 860326996-(Dimethoxythiophosphoryl)hexanoic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A solution of dimethylthiophosphite (4.56 g, 36.2 mmol), 6-bromohexanoic acid tert-butyl ester (100 g, 39.8 mmol) and triethylbenzylammonium chloride (0.82 g, 3.62 mmol) in dichloromethane (100 mL) was cooled on an ice bath and a solution of sodium hydroxide (14.5 g, 0.362 mol) in water (14.5 mL) was added slowly with vigorous stirring. The ice bath was removed and the mixture stirred for 3 days before being washed with water, dried (magnesium sulfate), and the solvent removed under reduced pressure to give crude 6-(dimethoxythiophosphoryl)hexanoic acid tert-butyl ester (8.00 g).

Workup

  1. customThe ice bath was removed
  2. washbefore being washed with water
  3. dry with materialdried (magnesium sulfate)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d2e8daade79b4195a1d79c927e61d125
Source dataset
uspto-grants-2005_09
Patent number
US06943267B1

Reaction notes

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