Diethyl Ether → HCID 58863700, compound

HRID 1352853Notes

Reaction equation

HRID 1352853 reaction equation
O[CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC>ClCCl>[Br:20][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58863612HCID 58863612, compound

Product 1

HCID 58863700HCID 58863700, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound (150 mg, 0.594 mmol) of Example 16-4 in dicloromethane (2 ml) were added carbon tetrabromide (207 mg, 0.623 mmol) and triphenylphosphine (163 mg, 0.623 mmol), and the mixture was stirred for 30 minutes at room temperature. By adding ether to the reaction mixture, the resulting precipitate was filtered off. The filtrate was concentrated and the residue was purified with silica gel chromatography (hexane:ethyl acetate=2:1) to give the subject compound (141 mg, 75.3%).

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified with silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e5a9bf57311c43138989688a0ae09b05
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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