Dichloromethane → Ethyl 4-carbamoyloxy-4-methyl-2-pentynoate

HRID 1032567Notes

Reaction equation

HRID 1032567 reaction equation
ClCCl.[OH:4][C:5]([CH3:14])([CH3:13])[C:6]#[C:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].ClS([N:19]=[C:20]=[O:21])(=O)=O>O>[C:20]([O:4][C:5]([CH3:13])([CH3:14])[C:6]#[C:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:21])[NH2:19]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70918Chlorosulfonyl isocyanateHCID 112289264-Hydroxy-4-methyl-pent-2-ynoic acid ethyl ester

Product 1

HCID 13343299Ethyl 4-carbamoyloxy-4-methyl-2-pentynoateYield 33.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml of a dichloromethane solution containing 4.9 g (31.4 millimoles) of ethyl 4-hydroxy-4-methyl-2-pentynoate, 3 ml (34.5 millimoles) of chlorosulfonyl isocyanate was added at a temperature of -10° C. The mixture was reacted for 30 minutes at -10° C. under stirring. The reaction mixture was returned to room temperature, and 20 ml of water was added thereto. The mixture was stirred for 15 minutes for hydrolysis treatment. The dichloromethane phase was separated by phase separation, washed with a 10% barium chloride solution and water successively, dried over sodium sulfate and then concentrated under reduced pressure, whereby 2.1 g (yield: 33%) of ethyl 4-carbamoyloxy-4-methyl-2-pentynoate in crystal form was obtained.

Workup

  1. additionwas added at a temperature of -10° C
  2. customThe mixture was reacted for 30 minutes at -10° C.
  3. customwas returned to room temperature
  4. stirringThe mixture was stirred for 15 minutes for hydrolysis treatment
  5. customThe dichloromethane phase was separated by phase separation
  6. washwashed with a 10% barium chloride solution and water successively
  7. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-026254d378124f59b88e255ca500b26c
Source dataset
uspto-grants-1990_09
Patent number
US04958024

Reaction notes

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