Tetrahydrofuran → 1-Phenyladamantane

HRID 476333Notes

Reaction equation

HRID 476333 reaction equation
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.C1COCC1.[C:17]1([Mg]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCC>[C:17]1([C:2]23[CH2:11][CH:6]4[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]4)[CH2:3]2)[CH2:9]3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 791061-BromoadamantaneHCID 178418255HCID 178418255, compound2×

Product 1

HCID 5226961-Phenyladamantane

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

1-Bromoadamantane (215.4 mg, 1.0 mmol) and a THF solution (1.55 mL, 0.97 M, 1.50 mmol) of phenylmagnesium bromide were used as starting materials, and reacted as in Entry 1. Conditions: The THF solution of phenylmagnesium bromide was added dropwise at 40° C. over 3 hours. After silica gel column chromatography (pentane), the title compound was obtained as a white solid (0.173 g, yield 81%).

Workup

  1. custommaterials, and reacted as in Entry 1

Sources & evidence

ORD record
ord-a3fdb770fdd04168ab93dbcbd9026371
Source dataset
uspto-grants-2014_01
Patent number
US08637710B2

Reaction notes

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