Triphenylphosphine → HCID 86728175, compound

HRID 1848377Notes

Reaction equation

HRID 1848377 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[NH:28][C:29](=[O:35])[C:30]([O:32][CH2:33][CH3:34])=O.[C:36]([O:44][CH3:45])(=[O:43])[C:37]#[C:38][C:39]([O:41][CH3:42])=[O:40]>C(Cl)CCl>[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[N:28]1[C:29](=[O:35])[C:30]([O:32][CH2:33][CH3:34])=[C:38]([C:39]([O:41][CH3:42])=[O:40])[CH:37]1[C:36]([O:44][CH3:45])=[O:43]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 12980Dimethyl acetylenedicarboxylateHCID 3908440HCID 3908440, compound

Product 1

HCID 86728175HCID 86728175, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of triphenylphosphine (629 mg, 2.40 mmol) and Intermediate 11A (458 mg, 2.00 mmol) in ClCH2CH2Cl (1 mL) was added dimethyl but-2-ynedioate (0.26 mL, 2.1 mmol) drop wise at rt. The reaction mixture was stirred at 80° C. in a capped vial for 18 h. The reaction mixture was allowed to cool to rt, loaded on to a 40 g silica gel column and purified with 0-100% EtOAc/Hex to give Intermediate 11B (560 mg, 1.58 mmol, 79.0% yield) as a slightly tan viscous oil. HPLC/MS (Method L) RT=1.77 min, [M+H]+ 356.0.

Workup

  1. temperatureto cool to rt
  2. custompurified with 0-100% EtOAc/Hex

Sources & evidence

ORD record
ord-a56e811d54cb47fc977b2a096da3e37f
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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