Hydrogen Peroxide → HCID 19753535, 화합물

HRID 1088019노트

반응식

HRID 1088019 반응식
[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

참가 물질

6

반응물 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 14794002HCID 14794002, 화합물

생성물 1

HCID 19753535HCID 19753535, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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 1 M 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(CDC13)δ1.1(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.

후처리

  1. temperaturecooled to -78~C under a nitrogen atmosphere
  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)

출처 및 근거

ORD 기록
ord-7e7949edac6c4e59a1f495a0986b17c9
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04960946

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