Tetrahydrofuran → HCID 10942917, compound

HRID 231931Notes

Reaction equation

HRID 231931 reaction equation
[CH2:1]1COCC1.[C:6]1([CH:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCN(CC)CC>C1(C)C=CC=CC=1>[C:6]1([CH:12]2[CH2:17][CH2:16][C:15](=[CH2:1])[CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 786054-Phenylcyclohexanone

Product 1

HCID 10942917HCID 10942917, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

BDAM (2.83 grams) was suspended in 40 milliliters of toluene and 2.2 milliliters of THF were added dropwise. After 10 minutes of stirring, 2.10 grams of 4-phenylcyclohexanone were added. The reaction mixture was refluxed for 1 hour and hydrolyzed with hydrated Ca(OH)2 in the presence of Et3N. After the usual work up, 0.21 grams of 4-phenyl-1-methylenecyclohexane was isolated (10% yield).

Sources & evidence

ORD record
ord-bac90a4f387942999a8e79c5be428819
Source dataset
uspto-grants-1989_07
Patent number
US04849574

Reaction notes

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