Oxygen → ethyl 2-(adamantan-1-yl)acetate

HRID 351327Notes

Reaction equation

HRID 351327 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].[CH:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[OH:18]N1C(=O)C2=CC=CC=C2C1=O.C(#N)C.O=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:8]12([CH2:3][CH:2]([OH:18])[C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[C:8]12([CH2:3][C:2](=[O:18])[C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[C:3]12([CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH2:16][CH:10]3[CH2:11][CH:12]([CH2:17][CH:8]([CH2:9]3)[CH2:15]1)[CH2:13]2

Participants

9

Reactant 5

HCID 977OxygenHCID 6342AcetonitrileHCID 8821Ethyl AcrylateHCID 9238AdamantaneHCID 10665N-Hydroxyphthalimide

Product 3

HCID 2795260ethyl 2-(adamantan-1-yl)acetateHCID 17798945HCID 17798945, compoundHCID 17798949HCID 17798949, compound

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Procedure

A mixture of 10 mmol of ethyl acrylate, 50 mmol of adamantane, 1 mmol of N-hydroxyphthalimide, 0.01 mmol of cobalt(II) acetate, 0.1 mmol of acetylacetonatocobalt(III), and 54 mmol of acetonitrile was stirred at 70° C. in an oxygen atmosphere (1 atm) for 8 hours. A reaction mixture was concentrated, and the concentrate was subjected to column chromatography on a silica gel to yield ethyl 3-(adamant-1-yl)-2-hydroxypropionate of the following formula (a), ethyl 3-(adamant-1-yl)-2-oxopropionate of the following formula (b), and ethyl 1-adamantaneacetate of the following formula (c) in yields of 55%, 16%, and 8%, respectively. The conversion rate from ethyl acrylate was 99%.

Workup

  1. concentrationA reaction mixture was concentrated

Sources & evidence

ORD record
ord-3faca7f0bfd44f1293e90cc3d06b9481
Source dataset
uspto-grants-2007_02
Patent number
US07183423B1

Reaction notes

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