4-Bromobutyryl chloride → HCID 19909509, compound

HRID 1534342Notes

Reaction equation

HRID 1534342 reaction equation
C([Li])(C)(C)C.[OH:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[Br:29][CH2:30][CH2:31][CH2:32][C:33](Cl)=[O:34]>CCCCC.O1CCCC1>[Br:29][CH2:30][CH2:31][CH2:32][C:33]([O:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:34]

Participants

6

Reactant 3

HCID 702254-Bromobutyryl chlorideHCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 178418306HCID 178418306, compound

Product 1

HCID 19909509HCID 19909509, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl lithium (a 1.7 M solution in pentane; 0.25 ml, 0.43 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (120.4 mg, 0.36 mmol) in tetrahydrofuran (6 ml) at 0° under argon. After 20 minutes, a solution of 4-bromobutyryl chloride (66 mg, 0.43 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued at room temperature for 16 hours and the mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (20×20 cm, 500μ silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a yellow oil.

Workup

  1. waitwas continued at room temperature for 16 hours
  2. customthe mixture was quenched with water
  3. extractionExtraction (ethyl ether) and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by preparative TLC (20×20 cm, 500μ silica plate; developed with 10% ethyl ether/hexane)

Sources & evidence

ORD record
ord-03f2e2504afe49889ff248c57108eea3
Source dataset
uspto-grants-1992_02
Patent number
US05089485

Reaction notes

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