Tetrahydrofuran → HCID 22650070, compound

HRID 1267552Notes

Reaction equation

HRID 1267552 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][C:7]1([OH:19])[CH:14]2[CH2:15][CH:10]3[CH2:11][C:12]([OH:17])([CH2:16][C:8]1([OH:18])[CH2:9]3)[CH2:13]2.C(N(CC)CC)C.C1COCC1>O>[C:1]([O:19][C:7]1([CH3:6])[CH:14]2[CH2:15][CH:10]3[CH2:11][C:12]([OH:17])([CH2:16][C:8]1([OH:18])[CH2:9]3)[CH2:13]2)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22650069HCID 22650069, compound

Product 1

HCID 22650070HCID 22650070, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A total of 6.5 mmole of acryloyl chloride was added dropwise to a mixture of 5 mmole of 2-methyl-1,2,5-adamantanetriol, 7.5 mmole of triethylamine and 50 ml of THF over about 15 minutes. After the completion of addition, the resulting mixture was stirred at room temperature for 1.5 hours. After the addition of water, the reaction mixture was extracted with ethyl acetate, the organic layer was concentrated, and the concentrate was subjected to column chromatography on a silica gel to thereby yield the title compound.

Workup

  1. additionAfter the completion of addition
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-140b4875af5a40758884bce00cb74053
Source dataset
uspto-grants-2003_04
Patent number
US06552143B2

Reaction notes

Loading…