4-Nitrophenyl chloroformate → HCID 69364094, compound

HRID 723762Notes

Reaction equation

HRID 723762 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][C@@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.Cl[C:11]([O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:12]>N1C=CC=CC=1>[C:11](=[O:12])([O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)[O:8][CH2:7][C@@H:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 736057(+)-Solketal

Product 1

HCID 69364094HCID 69364094, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(4S)-2,2-Dimethyl-1,3-dioxolan-4-ylmethanol (362 mg, 2.74 mM) was dissolved in pyridine (9 ml), stirred at ambient temperature, and treated in portions with 4-nitrophenyl chloroformate (552 mg, 2.74 mM). After 6 hours, solvent was evaporated, the residue redissolved in ethyl acetate (15 ml), washed with water (15 ml), sodium bicarbonate solution (15 ml), brine (15 ml), and dried (magnesium sulfate). Removal of the solvent gave the product as an oil sufficiently pure for further use (858 mg).

Workup

  1. customsolvent was evaporated
  2. dissolutionthe residue redissolved in ethyl acetate (15 ml)
  3. washwashed with water (15 ml), sodium bicarbonate solution (15 ml), brine (15 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-2d74d0ae3dd74c14a49de37c963d57f8
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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