Triethylamine → 2-Admantyl-4-methyl-phenyl ethyl carbonate

HRID 1915320Notes

Reaction equation

HRID 1915320 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[OH:24])[CH2:14]2.CCN(CC)CC>CN(C1C=CN=CC=1)C.ClCCl>[C:2](=[O:3])([O:4][CH2:5][CH3:6])[O:24][C:18]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=1[CH:8]1[CH:9]2[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:7]1[CH2:16]3)[CH2:15]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 226207762-Adamantyl-4-methylphenol

Product 1

HCID 666859302-Admantyl-4-methyl-phenyl ethyl carbonateYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl chloroformate (0.64 mL, 6.7 mmol) was added dropwise to a solution of 2-admantyl-4-methylphenol (1.09 g, 4.5 mmol), Et3N (1.25 mL, 9 mmol) and DMAP (catalytic amount) in dichloromethane (8 mL) cooled in an ice-water bath to 0° C. The mixture was allowed to warm to room temperature while stirring overnight, then filtered and the filtrate was concentrated. The residue was purified by column chromatography (10-20% ethyl acetate-hexanes) to yield 2-admantyl-4-methyl-phenyl ethyl carbonate as a yellow oil (1.32 g, 94%).

Workup

  1. temperatureto warm to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography (10-20% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-feea18967d7946b7a1cdfa80d5bcec3a
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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