Tetrahydrofuran → HCID 23435157, compound

HRID 2305277Notes

Reaction equation

HRID 2305277 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:7][C:8]([CH3:34])([C:10]12[CH2:19][C:14]3([O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[CH2:15][CH:16]([CH2:18][C:12]([O:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])([CH2:13]3)[CH2:11]1)[CH2:17]2)[OH:9].C(N(CC)CC)C.C1COCC1>O>[C:1]([O:9][C:8]([C:10]12[CH2:19][C:14]3([O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[CH2:15][CH:16]([CH2:18][C:12]([O:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])([CH2:13]3)[CH2:11]1)[CH2:17]2)([CH3:34])[CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 12010648HCID 12010648, compound

Product 1

HCID 23435157HCID 23435157, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A total of 30 mmole of methacrylic chloride was added dropwise to a mixture of 20 mmole of the above-prepared α,α-dimethyl-3,5-bis(2-methoxyethoxymethoxy)-1-adamantanemethanol, 40 mmole of triethylamine, and 80 ml of THF, over about 30 minutes. The resulting mixture was stirred at room temperature for 6 hours after the completion of addition. Water was added to the reaction mixture, and the resulting mixture was then extracted with ethyl acetate, the organic layer was concentrated, and the concentrate was subjected to column chromatography on a silica gel to yield 1-(1-methacryloyloxy-1-methylethyl)-3,5-bis(2-methoxyethoxymethoxy)adamantane.

Workup

  1. additionafter the completion of addition
  2. extractionthe resulting mixture was then extracted with ethyl acetate
  3. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-955806e1398d4e7598f29eb19c18e807
Source dataset
uspto-grants-2002_08
Patent number
US06440636B1

Reaction notes

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