Hydrogen Peroxide → HCID 19753535、化合物

HRID 483706ノート

反応式

HRID 483706 の反応式
[CH3:1][O:2][C:3]([CH3:14])(C)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[CH2:7]1.[CH:15]([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH-].[Na+].OO>O1CCCC1>[CH3:1][O:2][CH:3]([CH3:14])[CH2:4][CH:5]([CH3:15])[CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([OH:12])[CH2:7]1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 14794002HCID 14794002、化合物

生成物 1

HCID 19753535HCID 19753535、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3-(3-methoxy-3-methylbut-1-yl)cyclohexanone (1.4 g. 0.0051 mol) was dissolved in tetrahydrofuran (10 mL) and cooled to -78~C. under a nitrogen atmosphere with stirring. A solution of lithium tri-sec-butylborohydride (6.1 mL of a 1M solution of tetrahydrofuran, 0.0061 mol) was added. The mixture was allowed to come to 20~C. over 16 hours and 10% NaOH (aq, 4.0 mL) was added, followed by 30% hydrogen peroxide (aq, 4.0 mL). The mixture was extracted with hexane. The extracts were dried (Na2SO4) and concentrated to the residue which was purified by bulb to bulb distillation (air bath temp 175~C., 0.1 mm Hg) to yield 3-(3-methoxy-methylbut-1-yl)cyclohexanol as a mixture of diastereoisomers in the ratio of 94:6 (0.7 g). NMR(CDCl3)δ 1.1(s,6H), 1.2-1.8(m,13H), 3.2(s,3H), 4.1(brs,1H). IR (neat) 3410, 2990, 2960, 2870, 1460, 1370, 1110, 1090, 980 cm-1. MS (m/e) 43, 73, 109, 124, 143, 181, 201, 214.

後処理

  1. temperaturecooled to -78~C
  2. extractionThe mixture was extracted with hexane
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated to the residue which
  5. distillationwas purified by bulb to bulb distillation (air bath temp 175~C., 0.1 mm Hg)

出典と根拠

ORDレコード
ord-75c8f79c31e84c02ba41d4431360acc2
出典データセット
uspto-grants-1993_07
特許番号
US05225608

反応ノート

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