Diethyl Ether → HCID 54208735, compound

HRID 1732251Notes

Reaction equation

HRID 1732251 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH3:26])[CH2:11][CH2:12][CH2:13][C:14]([CH3:25])=[CH:15][CH2:16][CH2:17][C:18]([O:20][Si](C)(C)C)=[CH2:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[Br:32]N1C(=O)CCC1=O.CCOCC>O1CCCC1.[Cl-].[Na+].O>[CH2:1]([O:8][CH2:9][CH:10]([CH3:26])[CH2:11][CH2:12][CH2:13][C:14]([CH3:25])=[CH:15][CH2:16][CH2:17][C:18](=[O:19])[CH2:20][Br:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 516892Sodium Bicarbonate2×HCID 54158718HCID 54158718, compound

Product 1

HCID 54208735HCID 54208735, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

11-Benzyloxy-6,10-dimethyl-2-trimethylsiloxy-undec-1,5-diene (15.36 g, 41 mM) in dry tetrahydrofuran (400 ml) is treated with sodium bicarbonate (4.1 g, 49 mM) and N-bromosuccinimide (7.3 g, 41 mM) at -70° C. and allowed to stir for 4 hours. The reaction mixture is allowed to reach room temperature after which saturated sodium bicarbonate, ether and brine are added. The phases are separated, the aqueous phase is extracted with ether and the combined organic extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give crude 11-benzyloxy-1-bromo-6,10-dimethyl-2-oxo-undec-5-ene (17 g).

Workup

  1. customto reach room temperature
  2. additionare added
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ether
  5. washthe combined organic extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-9aa3ef8015ba44ce9737620a90e42643
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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