Sodium amide → HCID 57038220, compound

HRID 582752Notes

Reaction equation

HRID 582752 reaction equation
[Si:1]([O:18][C:19]1[CH2:23][CH:22](Br)[CH:21]([Br:25])[CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1C=CC=CC=1)[C:2]1C=CC=CC=1.[NH2-].[Na+].C(O[Na])(C)(C)C>O1CCCC1>[Si:1]([O:18][CH:19]1[CH2:23][CH:22]=[C:21]([Br:25])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 57103353HCID 57103353, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 57038220HCID 57038220, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution mixture of 4.5 g of 3,4-dibromocyclopenten-1-yl (t-butyldiphenylsilyl) ether and 50 ml of tetrahydrofuran were added at room temperature 910 mg of sodium amide and 3.25 g of t-butoxysodium, and the resulting mixture was stirred for 3.5 hours. The reaction liquid obtained was after-treated and purified in the same manner as in (1) of the intermediate preparation example 1 to obtain 2.53 g of (RS)-3-bromo-3-cyclopenten-1-yl (t-butyldimethylsilyl) ether. Yield 68%

Workup

  1. customThe reaction liquid
  2. customobtained
  3. additionwas after-treated
  4. custompurified in the same manner as in (1) of the intermediate preparation example 1

Sources & evidence

ORD record
ord-9b90f80d108149fd811738907aeb262c
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

Loading…