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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Dimethyl Sulfoxide → (S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octa-hydro-naphthalen-1-yl]-propionaldehyde

HRID 1604836
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인쇄 미리보기

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HRID 1604836 반응식
CS(C)=O.[C:5]([Si:9]([CH3:27])([CH3:26])[O:10][C@H:11]1[CH2:20][CH2:19][CH2:18][C@@:17]2([CH3:21])[C@H:12]1[CH2:13][CH2:14][CH:15]=[C:16]2[C@H:22]([CH3:25])[CH2:23][OH:24])([CH3:8])([CH3:7])[CH3:6].CCN(CC)CC>C(Cl)Cl.C(Cl)(=O)C(Cl)=O>[C:5]([Si:9]([CH3:27])([CH3:26])[O:10][C@H:11]1[CH2:20][CH2:19][CH2:18][C@@:17]2([CH3:21])[C@H:12]1[CH2:13][CH2:14][CH:15]=[C:16]2[C@H:22]([CH3:25])[CH:23]=[O:24])([CH3:7])([CH3:8])[CH3:6]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 21309369(S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-propan-1-ol

생성물 1

HCID 21310065(S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octa-hydro-naphthalen-1-yl]-propionaldehyde

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
3회
HCID 65578Oxalyl chloride용매

실험 절차

Swern reagent was prepared at -78° C. by adding slowly 1.6 ml of abs. DMSO, dissolved in 4 ml of CH2Cl2, to 0.908 ml of oxalylchloride in 26 ml of CH2Cl2.15 minutes later, 3.27 g of (S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-propan-1-ol (synthesis described in ref. Ex. 12) dissolved in 11 ml of CH2Cl2, were slowly added. After 0.3 h, 4.6 ml of NEt3 were added dropwise and the temperature allowed to reach -15° C. The reaction was quenched by pouring onto crushed ice/NH4Cl, extracted with ether, washed with water and brine, dried over magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=97/3) yielded (S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octa-hydro-naphthalen-1-yl]-propionaldehyde in nearly quantitative yield.

후처리

  1. additionby adding slowly 1.6 ml of abs
  2. additionwere slowly added
  3. customto reach -15° 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 magnesium sulfate
  10. customevaporated to dryness

출처 및 근거

ORD 기록
ord-ea7b3878decf4769bcd00191697fdfc8
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05994569

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