Water → (6-Methyl-1,3-dihydroisobenzofuran-5-yl)methanol

HRID 2047261ノート

反応式

HRID 2047261 の反応式
[Li].C(C1C=CC(C2C=CC(C(C)(C)C)=CC=2)=CC=1)(C)(C)C.[C:22]12[CH2:33][O:32][CH2:31][C:30]1=[CH:29][C:28]1[CH2:27][O:26][CH2:25][C:24]=1[CH:23]=2.O>O1CCCC1>[CH3:33][C:22]1[C:30]([CH2:31][OH:32])=[CH:29][C:28]2[CH2:27][O:26][CH2:25][C:24]=2[CH:23]=1

参加物

6

反応物 4

HCID 962WaterHCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylHCID 3028194LithiumHCID 595388301,3,5,7-Tetrahydrobenzo[1,2-c:4,5-c']difuran

生成物 1

HCID 86691253(6-Methyl-1,3-dihydroisobenzofuran-5-yl)methanol収率 30%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of lithium powder (15 g, 2.1 mol), 4,4′-di-tert-butylbiphenyl (5.0 g, 0.021 mol) and tetrahydrofuran (200 mL) was added a mixture of 5,11-dioxatricyclo[7.3.0.0^{3,7}]dodeca-1,3(7),8-triene (35 g, 0.21 mol) described in Production Example 1-4 and tetrahydrofuran (100 mL) at −78° C., followed by stirring at that temperature for 4 hours. Water (10 mol) was added at that temperature to the reaction mixture, and thoroughly stirred. The reaction mixture was allowed to warm to room temperature, and extracted with ethyl acetate after addition of a 2 N aqueous solution of hydrochloric acid (500 mL). The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7) to give the title compound (10 g, 30% yield).

後処理

  1. additionwas added
  2. stirringthoroughly stirred
  3. extractionextracted with ethyl acetate
  4. additionafter addition of a 2 N aqueous solution of hydrochloric acid (500 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7)

出典と根拠

ORDレコード
ord-0907c14d27a24928a1e50065e6f25dc8
出典データセット
uspto-grants-2013_11
特許番号
US08592470B2

反応ノート

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