Benzyl Bromide → HCID 19918600, compound

HRID 1755805Notes

Reaction equation

HRID 1755805 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([CH:4]1[CH:3]=[C:2]([CH3:1])[CH2:7][CH2:6][C:5]1=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 789134-Methylcyclohex-3-en-1-oneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 19918600HCID 19918600, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the above (18) (6.1 g) in dry THF (100 mL) at -78° C. was added a solution of lithium bis-trimethylsilylamide (50 ml, 1N in THF). The solution was stirred for 20 min then benzylbromide (30 mL) was added in one portion. The reaction was stirred for 6 h at -78° C. then allowed to slowly warm to room temperature. After evaporation of the solvent, the remaining mixture was taken up in hexane, washed with saturated NaCl, dried over MgSO4 and evaporated. The product (19) was obtained by flash chromatography on silica gel eluted with 2.5% ethyl acetate in hexane. (4.15 g, 39%): GC RT 7.29 min. (HP 530 mμ×20 m methylsilicone column, He carrier flow rate 20 mL/min., 100° C., 1 min. , 100°-180° C. 10° C./min.; TLC Rf 0.31 (5% ethyl acetate, n-hexane); 1H NMR (CDCl3) δ1.73(3H, br s), 2.2-3.3(7H, m), 5.35(1H, br s), 7.28(5H, m).

Workup

  1. stirringThe reaction was stirred for 6 h at -78° C.
  2. customAfter evaporation of the solvent
  3. washwashed with saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-7a4e18e22b2c405b93c22c18468dd01e
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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