Lithium Hexamethyldisilazide → methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate

HRID 1377749노트

반응식

HRID 1377749 반응식
C[C:2](P(OC)(O)=O)([C:4]([O-:6])=[O:5])[CH3:3].[CH3:12][Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:22]1([O:27][C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])C=O)[CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1>[CH3:12][O:6][C:4](=[O:5])/[CH:2]=[CH:3]/[C:30]1[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:28]([O:27][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:29]=1

참가 물질

5

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 53413272Trimethylphosphonoacetate

생성물 1

HCID 5702848methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of trimethylphosphonoacetate (13 mL, 82 mmol) in 36 mL of THF at 0° C. was added lithium bis(trimethylsilyl)amide (82 mL of 1M THF solution, 82 mmol). This solution was stirred for 20 min, and a solution of 3-cyclopentoxy-4-methoxybenzaldehyde (15 g, 68 mmol) in 30 mL of THF was then added dropwise via addition funnel. When reaction was judged complete by TLC analysis, the reaction was diluted with ethyl acetate:hexanes (1:1), and the organic layer was washed with H2O and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to afford (E)-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-prop-2-en-oate as a pale yellow solid (17.2 g, 92%). 1H-NMR (300 MHz): δ 3.79 (s, 3), 3.86 (s, 3), 6.28 (d, 1, J=16), 7.52 (d, 1, J=16).

후처리

  1. customWhen reaction
  2. washthe organic layer was washed with H2O and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1f5a32e51757451c82cec3f701473e82
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665754

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