3-Bromo-2-methyl-1-propene → HCID 22086395, compound

HRID 2227272Notes

Reaction equation

HRID 2227272 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])[CH2:15][CH2:16][CH2:17][C:18]1([CH3:23])[O:22][CH2:21][CH2:20][O:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+].Br[CH2:38][C:39]([CH3:41])=[CH2:40]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])[C@@H:15]([CH2:16][CH2:17][C:18]1([CH3:23])[O:19][CH2:20][CH2:21][O:22]1)[CH2:40][C:39]([CH3:41])=[CH2:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 22086394HCID 22086394, compoundHCID 86588160Lithim bis(trimethylsilylamide)

Product 1

HCID 22086395HCID 22086395, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-2 (18 g, 54 mmol) in tetrahydrofuran (400 mL) at −78° C. under argon was added a solution of lithium bis(trimethylsilylamide) (70.2 mL of a 1.0 M solution in tetrahydrofuran) over 20 min. After an additional 20 min., 3-bromo-2-methylpropene (14.6 g, 108 mmol) was added in one portion. After 20 min., the reaction mixture was allowed to warm to 0° C. After 3.5 h, the reaction mixture was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated at reduced pressure. The resulting oil (3-1) was used without further purification.

Workup

  1. waitAfter 20 min.
  2. waitAfter 3.5 h
  3. washwashed with water, saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting oil (3-1) was used without further purification

Sources & evidence

ORD record
ord-43d4f223c6f94608834a7f2a5edff178
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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