Triphenylphosphine → HCID 58841188, compound

HRID 1269364Notes

Reaction equation

HRID 1269364 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:20]Br.CCN(C(C)C)C(C)C.O[CH2:32][C:33]1[CH:34]=[C:35]([CH:63]=[CH:64][CH:65]=1)[O:36][C:37]([O:39][CH2:40]/[C:41](/[C:53]1[CH:58]=[CH:57][C:56]([S:59]([CH3:62])(=[O:61])=[O:60])=[CH:55][CH:54]=1)=[C:42](/[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)\[C:43]([O:45][CH3:46])=[O:44])=[O:38]>C(Cl)Cl>[Br:20][CH2:32][C:33]1[CH:34]=[C:35]([CH:63]=[CH:64][CH:65]=1)[O:36][C:37]([O:39][CH2:40]/[C:41](/[C:53]1[CH:58]=[CH:57][C:56]([S:59]([CH3:62])(=[O:61])=[O:60])=[CH:55][CH:54]=1)=[C:42](/[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)\[C:43]([O:45][CH3:46])=[O:44])=[O:38]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24408BromineHCID 81531DiisopropylethylamineHCID 58841175HCID 58841175, compound

Product 1

HCID 58841188HCID 58841188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 470 mg of Ph3P in 15 mL of CH2Cl2 cooled at 0° C. was added 1.75 mL of a 1.0M Br2 solution in CH2Cl2. After 10 min, 340 μL of Hunig's base was added followed by 798 mg of methyl (2Z)-4-({[3-(hydroxymethyl)phenoxy]carbonyl}oxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoate dissolved in 20 mL of CH2Cl2. After 15 min at 0° C., the reaction mixture was warmed to rt for 1 h. The reaction was quenched with H2O, extracted twice with EtOAc and washed with brine, dried over sodium sulfate, evaporated, and purified by flash chromatography (10–50% EtOAc/hexane) to afford 786 mg of the title compound as a colorless oil.

Workup

  1. waitAfter 15 min at 0° C.
  2. customThe reaction was quenched with H2O
  3. extractionextracted twice with EtOAc
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. custompurified by flash chromatography (10–50% EtOAc/hexane)

Sources & evidence

ORD record
ord-ee0639e64e8c491397160e52eb131f9c
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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