Water → 548-42-5

HRID 231699Notes

Reaction equation

HRID 231699 reaction equation
Br[C:2]1[N:16]([Si](C(C)(C)C)(C)C)[C:15]2[C:24]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([CH3:25])[CH2:7][N:6]1[CH3:26].C([Li])(C)(C)C.CCCCCC.O>C1(C)C=CC=CC=1>[CH3:26][N:6]1[C@H:5]2[C@@H:10]([C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:24]=3[C:3]([CH2:4]2)=[CH:2][NH:16]4)[CH:9]=[C:8]([CH3:25])[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 15292888HCID 15292888, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 73484548-42-5

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-90 °C

Procedure

800 mg of 2-bromo-1-(tert-butyldimethylsilyl)-8,9-didehydro-6,8-dimethylergoline was dissolved in 50 ml of anhydrous toluene; the solvent was distilled off under vacuum and the mixture taken up in 75 ml of anhydrous, freshly distilled toluene under an argon atmosphere. To this solution was added 1 ml of anhydrous tetramethylethylenediamine and the mixture was cooled to -90° C. Then the mixture was combined with 6.0 ml of 1.4-molar tert-butyllithium solution in hexane (8.4 mmol) and agitated for 5 hours. Water was then added, the mixture was extracted with methylene chloride, the organic phase was dried with sodium sulfate and evaporated. In a quantitative yield, 8,9-didehydro-6,8-dimethylergoline was isolated. The desired 8,9-didehydro-6,8-dimethyl-2-trimethylsilylergoline could not be detected by NMR.

Workup

  1. distillationthe solvent was distilled off under vacuum
  2. additionTo this solution was added 1 ml of anhydrous tetramethylethylenediamine
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d89ed78284394e98b32740f37b74dac8
Source dataset
uspto-grants-1989_07
Patent number
US04847262

Reaction notes

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