Sodium Sulfite → 3-(1-(Tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol

HRID 253138노트

반응식

HRID 253138 반응식
[CH2:1]([C:4]1([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH2:7][CH2:6][CH2:5]1)C=C.O.CC([OH:21])(C)C.C[N+]1([O-])[CH2:28][CH2:27][O:26]CC1.S([O-])([O-])=O.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.O>[Si:9]([O:8][C:4]1([CH2:1][CH:27]([OH:26])[CH2:28][OH:21])[CH2:7][CH2:6][CH2:5]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

참가 물질

7

반응물 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 66844818(1-Allylcyclobutoxy)(tert-butyl)dimethylsilaneHCID 714019492-Methylpropan-2-ol--water (1/1)

생성물 1

HCID 668451483-(1-(Tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 962Water용매

실험 절차

To a 2 L round bottomed flask was added (1-allylcyclobutoxy) (tert-butyl)dimethylsilane (previous step) and H2O/t-BuOH (1:1, 1 L). NMO (32.68 g, 279 mmol) was added to the mixture. After stirring for 5 min the solution was found to be homogenous. Osmium tetroxide (1.00 g, 3.93 mmol) was added and the reaction was stirred at RT. After 2 h, TLC revealed the reaction to be complete. 500 mL of H2O and sodium sulfite (19.5 g, 155 mmol) were added and the reaction was stirred for another hour. The aqueous solution was extracted with ether (2×1 L). The combined organics were concentrated in vacuo to give 3-(1-(tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol, as a light yellow oil. The oil contained some t-BuOH, but was carried forward without further purification.

후처리

  1. stirringthe reaction was stirred at RT
  2. waitAfter 2 h
  3. customthe reaction
  4. stirringthe reaction was stirred for another hour
  5. extractionThe aqueous solution was extracted with ether (2×1 L)
  6. concentrationThe combined organics were concentrated in vacuo

출처 및 근거

ORD 기록
ord-aa5b1e4ea92b4414a0676c8fc3e8f0ff
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872009B2

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