Ethanol → HCID 15338401, compound

HRID 1740265Notes

Reaction equation

HRID 1740265 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([Cl:25])([Cl:24])[C:21]([OH:23])=[O:22].C(O)C.C(N(CC)CC)C>CN(C)C=O.ClCCl.O>[CH2:1]([O:22][C:21](=[O:23])[C:20]([Cl:24])([Cl:25])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][Br:7])[CH3:2]

Participants

8

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15338400HCID 15338400, compound

Product 1

HCID 15338401HCID 15338401, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

One drop of dimethylformamide and 1.34 g (10.5 mmol) oxalyl chloride was added to a solution of 3.30 g (8.77 mmol) 2 in 40 ml dichloromethane. After 30 minutes excess oxalyl chloride was removed in a stream of nitrogen. Subsequently a mixture of 0.97 g (21.1 mmol) ethanol and 2.13 g (21.1 mmol) triethylamine was added dropwise at 0° C. It was allowed to reach room temperature and it was stirred for a further 30 minutes. After adding 60 ml water it was extracted with methylene chloride, washed with 0.5 N HCl and water, dried over sodium sulfate and the solvent was removed. Yield 3.38 g (95%) colourless oil.

Workup

  1. customAfter 30 minutes excess oxalyl chloride was removed in a stream of nitrogen
  2. additionwas added dropwise at 0° C
  3. customto reach room temperature
  4. extractionwas extracted with methylene chloride
  5. washwashed with 0.5 N HCl and water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-bdef6aa5d8474921977b6097eca27b60
Source dataset
uspto-grants-1999_10
Patent number
US05968982

Reaction notes

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