Tetrahydrofuran → HCID 22650052, compound

HRID 2305274Notes

Reaction equation

HRID 2305274 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[OH:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][C:9]([C:17]([CH3:20])([CH3:19])[OH:18])([CH2:10]3)[CH2:8]1)[CH2:14]2.C(N(CC)CC)C.O1CCCC1>O>[C:1]([O:18][C:17]([C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:16][C:7]([OH:6])([CH2:14]3)[CH2:8]1)[CH2:10]2)([CH3:20])[CH3:19])(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 14439059HCID 14439059, compound

Product 1

HCID 22650052HCID 22650052, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A total of 10 mmole of acrylic chloride was added dropwise to a mixture of 10 mmole of the above-prepared 3-hydroxy-α,α-dimethyl-1-adamantanemethanol, 10 mmole of triethylamine, and 40 ml of tetrahydrofuran ,over about 30 minutes. After the completion of addition, the resulting mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture and the mixture was concentrated, and the concentrate was subjected to column chromatography on a silica gel to yield the title compound in a yield of 23%.

Workup

  1. additionAfter the completion of addition
  2. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-43c0cf58aa55472a87ef6e95bc530db7
Source dataset
uspto-grants-2002_08
Patent number
US06440636B1

Reaction notes

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