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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
Notes
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Reaction equation

HRID 1604836 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
3×
HCID 65578Oxalyl chlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ea7b3878decf4769bcd00191697fdfc8
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05994569

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes