Chloroacetyl chloride → HCID 13598223, compound

HRID 1601451Notes

Reaction equation

HRID 1601451 reaction equation
[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[Cl:15][CH2:16][C:17](Cl)=[O:18]>ClCCl>[Cl:15][CH2:16][C:17]([O:5][CH2:4][CH2:3][Si:2]([CH3:7])([CH3:6])[CH3:1])=[O:18]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanol

Product 1

HCID 13598223HCID 13598223, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 2-(trimethylsilyl)ethanol (7.3 mL) and triethylamine (25 mL) in dichloromethane (80 mL). Cool in an ice bath. Add dropwise chloroacetyl chloride (6.9 g). After the addition is complete warm the reaction mixture to ambient temperature After 5 hours, add chloroacetyl chloride (2.8 g), After 2 hours, filter the reaction mixture and extract with a saturated aqueous solution of sodium bicarbonate and then water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Distill the residue to give 2-(trimethylsilyl)ethyl chloroacetate: bp 150° C. at 28 mm of Hg.

Workup

  1. temperatureCool in an ice bath
  2. additionAfter the addition
  3. filtrationfilter the reaction mixture
  4. extractionextract with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue
  9. distillationDistill the residue

Sources & evidence

ORD record
ord-96a7591d8f204c26a645660d110c0d6d
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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