Benzyl Bromide → HCID 54466557, compound

HRID 1755816Notes

Reaction equation

HRID 1755816 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.C(OCC)(=O)C>[CH2:31]([CH:18]1[CH:19]=[C:14]([C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH3:13])[CH2:15][CH2:16][C:17]1=[O:20])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 53922310HCID 53922310, compound

Product 1

HCID 54466557HCID 54466557, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of the above ketone (33) (14.93 g) in dry THF (200 mL) at -78° C. under Ar was added a solution of lithium bis-trimethylsilylamide (55 mL, 1N in THF). After stirring for 20 min benzylbromide (35 mL) was added and the reaction stirred for an additional 6 h at -78° C. then allowed to slowly warm to room temperature. The reaction was taken up in ethyl acetate, washed with 1N HCl, saturated NaCl, dried over MgSO4 and evaporated. The product (34) was obtained by flash chromatography on silica gel eluted with 20 to 25% ethyl acetate in n-hexane (6.09 g, 31%): TLC Rf 0.17 (20% ethyl acetate, n-hexane); 1H NMR (CDCl3) δ1.12 (3H, d, J=7 Hz), 2.0-3.2 (7H, m), 4.18(1H, q), 5.1(2H, s), 5.33(1 H, dd), 5.55(1H, br s), 7.22 (5H, m), 7.32 (5H, s).

Workup

  1. additionwas added
  2. temperatureto slowly warm to room temperature
  3. washwashed with 1N HCl, saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-a14048f7f3514d92b5c8c527c6d6f62f
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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