Imidazole → [5-Bromo-1-(1-propylcyclobutyl)pent-3-enyloxy]tert-butyldimethylsilane

HRID 2080907Notes

Reaction equation

HRID 2080907 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[Si:27]([O:34][CH:35]([C:41]1([CH2:45][CH2:46][CH3:47])[CH2:44][CH2:43][CH2:42]1)[CH2:36][CH:37]=[CH:38][CH2:39]O)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>C(Cl)Cl.CCCCCC>[Br:1][CH2:39][CH:38]=[CH:37][CH2:36][CH:35]([C:41]1([CH2:45][CH2:46][CH3:47])[CH2:44][CH2:43][CH2:42]1)[O:34][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 671021205-(Tert-butyldimethylsilanyloxy)-5-(1-propylcyclobutyl)pent-2-en-1-ol

Product 1

HCID 67101903[5-Bromo-1-(1-propylcyclobutyl)pent-3-enyloxy]tert-butyldimethylsilaneYield 86.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

Bromine (0.17 mL, 3.22 mmol) was added to a solution of triphenylphosphine (844 mg, 3.22 mmol) and imidazole (219 mg, 3.22 mmol) in CH2Cl2 (11.0 mL) at 23° C. After 0.5 h a solution of the alcohol 7 (838 mg, 2.68 mmol) in CH2Cl2 (2.7 mL) was added. The reaction was stirred for 1 h, diluted with hexane and then filtered through celite. The filtrate was concentrated in vacuo and purified by FCC (silica gel, 100% hex) to give 870 mg (86%) of the bromide 8 as a clear, light yellow oil.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by FCC (silica gel, 100% hex)

Sources & evidence

ORD record
ord-7e157f8a12c24fe8bc362984e8d44716
Source dataset
uspto-grants-2011_04
Patent number
US07932420B2

Reaction notes

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