Tetrahydrofuran → HCID 22650070, compound

HRID 2120523Notes

Reaction equation

HRID 2120523 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 acrylyl 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 adding 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-4cebd77503884e72be2dbdbc604c0848
Source dataset
uspto-grants-2004_02
Patent number
US06692889B1

Reaction notes

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