TMS-Imidazole → HCID 86754890, compound

HRID 1604839Notes

Reaction equation

HRID 1604839 reaction equation
[OH:1][C:2]([CH3:23])([CH3:22])/[CH:3]=[CH:4]/[CH:5]=[CH:6]/[CH2:7][C@H:8]([C:10]1[C@:11]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][CH:19]=1)[C:15](=[O:20])[CH2:14][CH2:13][CH2:12]2)[CH3:9].[Si:24](C1NC=CN=1)([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[CH3:9][C@@H:8]([C:10]1[C@:11]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][CH:19]=1)[C:15](=[O:20])[CH2:14][CH2:13][CH2:12]2)[CH2:7]/[CH:6]=[CH:5]/[CH:4]=[CH:3]/[C:2]([CH3:22])([O:1][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH3:23]

Participants

4

Reactant 2

HCID 14420972TMS-ImidazoleHCID 86754891HCID 86754891, compound

Product 1

HCID 86754890HCID 86754890, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

420 mg of (4aS,8aR)-5-((3E,5E)-(R)-7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)-4a-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one were reacted at RT with 0.389 ml of TMS-imidazole (2 equivalents) in 1.3 ml of CH2Cl2. After 20 hours the mixture was poured onto crushed ice, extracted with ether, washed with brine, dried over magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=95/5) yielded 463 mg of (4aS,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one as colourless oil.

Workup

  1. additionAfter 20 hours the mixture was poured
  2. customonto crushed ice
  3. extractionextracted with ether
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0682cf498ca94cfb89f9801424bdd7a8
Source dataset
uspto-grants-1999_11
Patent number
US05994569

Reaction notes

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