Tetrahydrofuran → 10-Bromo-undecan-1-ol

HRID 53499Notes

Reaction equation

HRID 53499 reaction equation
[Br:1][CH:2]([CH3:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12].C1COCC1.B.C1COCC1.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O>[Br:1][CH:2]([CH3:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 54340110-Bromoundecanoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 1183187010-Bromo-undecan-1-olYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask containing 10-bromoundecanoic acid (25.0 g, 94.2 mmol) was charged with dry THF (250 ml), immersed in an ice/water bath and fitted with an addition funnel. The addition funnel was charged with borane- THF solution (1.0M, 113 ml, 113 mmol) which was added to the stirred reaction mixture over a period of 45 minutes. 3 hrs after the addition was completed, the reaction was poured into a stirred mixture of EtOAc (500 ml) and 10% aqueous potassium carbonate (300 ml). After vigorously stirring for 0.5 hr, the layers were separated. The organic phase was washed with water (250 ml) and brine (250 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:4; EtOAc:hexanes) provided 10-bromo-undecan-1-ol (20.8 g, 88% ).

Workup

  1. customimmersed in an ice/water bath
  2. customfitted with an addition funnel
  3. additionwas added to the stirred reaction mixture over a period of 45 minutes
  4. addition3 hrs after the addition
  5. customthe layers were separated
  6. washThe organic phase was washed with water (250 ml) and brine (250 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-68df45de7e694a148e8e0bad9afa2982
Source dataset
uspto-grants-1997_04
Patent number
US05620677

Reaction notes

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