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

HRID 1377749ノート

反応式

HRID 1377749 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1f5a32e51757451c82cec3f701473e82
出典データセット
uspto-grants-1997_09
特許番号
US05665754

反応ノート

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