Chlorotrimethylsilane → Adamantanone

HRID 2084561Notes

Reaction equation

HRID 2084561 reaction equation
CC1O[C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2N=1.C(N([CH:18]([CH3:20])[CH3:19])C(C)C)C.[CH3:21][Si](Cl)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[CH:10]12[CH2:4][CH:5]3[CH2:19][CH:18]([CH2:20][CH:8]([CH2:7]3)[C:9]1=[O:11])[CH2:21]2

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 81531DiisopropylethylamineHCID 6765042-Methyl-1,3-benzoxazol-6-olHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 64151Adamantanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.6 g 2-methyl-benzoxazol-6-ol (formula IIb) in 100 ml of dry tetrahydrofuran, cooled to 0°, N-ethyldiisopropylamine and trimethylsilyl chloride are added. The mixture is stirred at room temperature for about 2 hours, cooled to −78°, and sodium bis(trimethylsilyl)amide solution is added in portions. To the mixture obtained solid 2-adamantanone (formula VI) is added and the mixture is kept at −78° for about one hour. The reaction mixture is allowed to warm up to room temperature and is pointed into 300 ml of 1 M NaHSO4 solution. The mixture is extracted with ethyl acetate and the organic layer is dried over sodium sulfate. The solvent is evaporated off and the residue is purified by chromatography. The above title compounds are obtained (m.p., respectively, 248-253° and 238-240°).

Workup

  1. temperaturecooled to −78°

Sources & evidence

ORD record
ord-1ab27609abe54dd5b259b75f1c9f0b4b
Source dataset
uspto-grants-2004_04
Patent number
US06716865B1

Reaction notes

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