Tetrahydrofuran → HCID 22650057, compound

HRID 393355Notes

Reaction equation

HRID 393355 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH2:6]([C:8]([CH3:20])([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)[OH:9])[CH3:7].C(N(CC)CC)C.O1CCCC1>O>[C:1]([O:9][C:8]([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)([CH3:20])[CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 13779141HCID 13779141, compound

Product 1

HCID 22650057HCID 22650057, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A total of 10 mmole of acryloyl chloride was added dropwise to a mixture of 10 mmole of the above-prepared α-ethyl-α-methyl-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. After the addition of water, the reaction mixture was concentrated, and the concentrate was subjected to column chromatography on a silica gel to thereby yield the title compound in a yield of 74%.

Workup

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

Sources & evidence

ORD record
ord-be87e2192c9146008c3974ec71564304
Source dataset
uspto-grants-2004_10
Patent number
US06806335B2

Reaction notes

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