Tetrahydrofuran → HCID 10942917, compound

HRID 2232681Notes

Reaction equation

HRID 2232681 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>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

4

Reactant 2

HCID 8028TetrahydrofuranHCID 786054-Phenylcyclohexanone

Product 1

HCID 10942917HCID 10942917, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

BDAM (3.00 grams) was suspended in 40 milliliters of toluene and 2 molar equivalents of THF were added at 0° C. After a homogeneous solution was formed, 1 molar equivalent (2 milliliters) of TEAL was added. After 10 minutes of stirring, 2.50 grams of 4-phenylcyclohexanone were added. After 3 hours of stirring the reaction mixture was hydrolyzed and worked up as described in Example 1. A total of 1.93 grams of 4-phenyl-1-methylenecyclohexane was isolated (78% yield).

Workup

  1. customAfter a homogeneous solution was formed
  2. addition1 molar equivalent (2 milliliters) of TEAL was added
  3. stirringAfter 3 hours of stirring the reaction mixture

Sources & evidence

ORD record
ord-7a30970bbac2480497ebdc041fef39fd
Source dataset
uspto-grants-1988_11
Patent number
US04788367

Reaction notes

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