Diethyl Ether → HCID 20688053, compound

HRID 1596816Notes

Reaction equation

HRID 1596816 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.[C:11]([C:15]1([C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:17][O:16]1)([CH3:14])([CH3:13])[CH3:12].C(OCC)C>CCCCC.CN(P(N(C)C)(N(C)C)=O)C>[C:11]([C:15]([OH:16])([CH2:17][C:1]#[C:2][CH2:3][CH2:4][CH3:5])[C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 123091-PentyneHCID 3293992,2-ditert-butyloxiraneHCID 178418339Butyllithium

Product 1

HCID 20688053HCID 20688053, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 12679HexamethylphosphoramideSolvent2×

Procedure

1.26 ml (12.8 mmol) 1-pentyne were added dropwise at 0° C. under argon for 5 minutes to 8.0 ml (12.8 mmol) of a 1.6-molar n-butyllithium solution in pentane. The solution obtained was cooled for another 15 minutes, and then the solvent was withdrawn under reduced pressure. 5 ml HMPA and a solution of 1.0 g (6.4 mmol) 2,2-di-tert-butyloxirane in 2 ml HMPA were added. The reaction solution was stirred for 20 hours at room temperature. Subsequently, it was processed analogous to Example 1. The raw product obtained was cleaned by means of a silica column with 2% diethyl ether/light gasoline. There were obtained 1.21 g (84%) 3-tert-butyl-2,2-dimethylnon-5-in-3-ol

Workup

  1. customThe solution obtained
  2. temperaturewas cooled for another 15 minutes
  3. customthe solvent was withdrawn under reduced pressure
  4. customThe raw product obtained

Sources & evidence

ORD record
ord-078e20830dac494285372dda7a6ff218
Source dataset
uspto-grants-2001_09
Patent number
US06291713B1

Reaction notes

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