Diethyl Ether → HCID 15447926, compound

HRID 900771Notes

Reaction equation

HRID 900771 reaction equation
Br[CH:2]([CH2:18]Br)[C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5].C(O[K])(C)(C)C.CCOCC.[NH4+].[Cl-]>C1COCC1>[C:12]1([C:3]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)([C:2]#[CH:18])[C:4]#[N:5])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 69293740HCID 69293740, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 15447926HCID 15447926, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3,4-dibromo-2,2-diphenylbutanenitrile 45 (7.5 g, 19.8 mmol) in THF (50 ml) was added dropwise to a suspension of tert-BuOK (11.1 g, 99 mmol) in THF (250 ml) at −78° C. After 1 h30, the brown mixture was poured into a mixture of ether and a saturated aqueous NH4Cl solution. After separation, the organic phase was washed twice with water and finally with brine. Drying over MgSO4 and evaporation gave an brown-orange oil which was chromatographied over silica gel (CH2Cl2/Hexane 25/75). The alkyne 46 was obtained as a slightly yellow oil (4 g, 93%).

Workup

  1. customAfter separation
  2. washthe organic phase was washed twice with water and finally with brine
  3. dry with materialDrying over MgSO4 and evaporation
  4. customgave an brown-orange oil which

Sources & evidence

ORD record
ord-ab173883a02e4a79b377e1c897fd5508
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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