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Dimethyl Sulfoxide → (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde

HRID 1604831
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HRID 1604831 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([Si:15]([CH3:33])([CH3:32])[O:16][C@H:17]1[CH2:26][CH2:25][CH2:24][C@@:23]2([CH3:27])[C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:22]2[C@H:28]([CH3:31])[CH2:29][OH:30])([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC>C(Cl)Cl>[C:11]([Si:15]([CH3:33])([CH3:32])[O:16][C@H:17]1[CH2:26][CH2:25][CH2:24][C@@:23]2([CH3:27])[C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:22]2[C@H:28]([CH3:31])[CH:29]=[O:30])([CH3:13])([CH3:14])[CH3:12]
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6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21309368(S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol

생성물 1

HCID 57255936(S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Swern reagent was prepared at -70° C. by adding slowly 1.70 ml of abs. DMSO to 0.947 ml of oxalylchloride, dissolved in 27 ml of CH2Cl2. 15 minutes later, 3.43 g of (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol (synthesis described in ref. Ex. 12), dissolved in 10 ml of CH2Cl2, were slowly added. After 0.25 h, 4.8 ml of NEt3 were added dropwise and the temperature allowed to reach -30° C. The reaction was quenched by pouring onto crushed ice/NH4Cl, extracted with ether, washed with water and brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=97/3) afforded (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde as colourless oil.

후처리

  1. additionby adding slowly 1.70 ml of abs
  2. additionwere slowly added
  3. customto reach -30° C
  4. customThe reaction was quenched
  5. additionby pouring
  6. customonto crushed ice/NH4Cl
  7. extractionextracted with ether
  8. washwashed with water and brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated to dryness

출처 및 근거

ORD 기록
ord-55f9ec093515472fabad034178d38f04
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05994569

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