Benzyl iodide → HCID 11160280, 화합물

HRID 130563

반응식

HRID 130563 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][CH:12]([C@H:14]1[CH2:19][O:18][C:16](=[O:17])[CH2:15]1)[CH3:13].[CH2:20](I)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:20]([C@@H:15]1[C@@H:14]([CH:12]([CH3:13])[CH3:11])[CH2:19][O:18][C:16]1=[O:17])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 12098Benzyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 11083905(S)-beta-(2-propyl)-gamma-butyrolactone

생성물 1

HCID 11160280HCID 11160280, 화합물수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 92 mL, 92 mmol) was added in 3-5 minutes to a solution of (S)-β-(2-propyl)-γ-butyrolactone 175 (11.68 g, 91.25 mmol) in dry THF 100 mL at −78° C. under argon atmosphere. It was stirred for 1 h and a solution of benzyl iodide (21.87 g, 100.37 mmol )in dry THF was added rapidly. Stirring was continued for 1.5 hours and quenched at −78° C. by the addition of a solution of brine followed by ethyl acetate. The organic phase was separated and the aqueous was further extracted with ether. Chromatography on silica gel first eluted with 5% methylene chloride in pet ether, and finally with 10% ether in pet ether gave desired compound 11.6 g, 58%. NMR (CDCl3) δ 7.19 (m, 5H, C6H5), 4.02 (app. t, 1H, CHaHbO), 3.87 (dd, 1H, CHaHbO), 2.98 (d, 2H, ArCH2), 2.57 (q, 1H, BnCHC═O), 2.05 (m, 1H, CHCH(Me)2, 1.55 (m, 1H, CH(Me)2), 0.81 (d, 3H, CH3) and 0.72 (d, 3H, CH3).

후처리

  1. stirringStirring
  2. waitwas continued for 1.5 hours
  3. customquenched at −78° C. by the addition of a solution of brine
  4. customThe organic phase was separated
  5. extractionthe aqueous was further extracted with ether
  6. washChromatography on silica gel first eluted with 5% methylene chloride in pet ether

출처 및 근거

ORD 기록
ord-0f055982e9ea44dfaa6392f0b6ca3e38
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381747B2

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