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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
ノート
印刷プレビュー

反応式

HRID 1604836 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
3 回
HCID 65578Oxalyl chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ea7b3878decf4769bcd00191697fdfc8
出典データセット
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05994569

反応ノート

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