Water → HCID 86633686, compound

HRID 1009319Notes

Reaction equation

HRID 1009319 reaction equation
[NH2:1][CH2:2][CH:3]([OH:7])/[CH:4]=[CH:5]/[CH3:6].C(N(C(C)C)CC)(C)C.[CH3:17][O:18][C:19](Cl)=[O:20].O>ClCCl>[CH3:17][O:18][C:19](=[O:20])[NH:1][CH2:2][CH:3]([OH:7])/[CH:4]=[CH:5]/[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 13123254HCID 13123254, compound

Product 1

HCID 86633686HCID 86633686, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(E)-1-Amino-3-penten-2-ol (1.3 g, 12.9 mmol) (Overman, L. E. in J. Am. Chem. Soc. 55, 22, 1983, 6622-6629) and diisopropylethylamine (2.7 mL, 15.4 mmol) were dissolved in dichloromethane (20 mL). Methylchloroformate (1 mL, 12.9 mmol) was added slowly and the mixture was stirred a 0° C. for 2 h. Water (25 mL) was added and the phases separated. Extraction with dichloromethane (3×25 mL), drying, filtration and evaporation gave the crude product ((E)-2-hydroxy-pent-3-enyl)carbamic acid methyl ester (2.1 g, 100%) as a yellow oil.

Workup

  1. customthe phases separated
  2. extractionExtraction with dichloromethane (3×25 mL)
  3. customdrying
  4. filtrationfiltration and evaporation

Sources & evidence

ORD record
ord-940ed6d100fa41758065c2a5d3b0e24c
Source dataset
uspto-grants-2011_07
Patent number
US07973082B2

Reaction notes

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