Benzoyl chloride → HCID 70005219, compound

HRID 1860528Notes

Reaction equation

HRID 1860528 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[CH3:26][O:27][C:28](=[O:56])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C@H:35]1[C@H:39]([CH:40]=[CH:41][Sn](CCCC)(CCCC)CCCC)[CH2:38][CH2:37][C:36]1=[O:55]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:26][O:27][C:28](=[O:56])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C@H:35]1[C@H:39]([CH:40]=[CH:41][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:38][CH2:37][C:36]1=[O:55]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 521585Tris(furan-2-yl)phosphaneHCID 70006201HCID 70006201, compound

Product 1

HCID 70005219HCID 70005219, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzoyl chloride (0.224 mL, 1.94 mmol) in tetrahydrofuran (20 mL) was added tris(dibenzylideneacetone)dipalladium(0) (Pd2(DBA)3) (8.8 mg, 0.01 mmol) and tri-2-furylphosphine (9.2 mg, 0.04 mmol). The mixture was stirred for 10 minutes and trans-7-[2-oxo-5-(2-tributylstannanyl-vinyl)-cyclopentyl]-heptanoic acid methyl ester (the compound of Preparation 1, Step D, 1.0 g, 1.85 mmol) was added. The reaction was stirred for 24 h and was concentrated in vacuo. Radial chromatography (hexanes to 20% hexanes in ethyl acetate) provided the title compound of Step A as a clear and colorless oil (569 mg). 1H NMR (CDCl3, 250 MHz) d 7.94 (m, 2H), 7.62-7.42 (m, 3H), 7.00 (m, 2H), 3.64 (s, 3H), 2.75 (m, 1H), 2.44 (m, 1H), 2.23 (m, 5H), 2.03 (m, 1H), 1.86-1.16 (m, 8H), 0.90 (t, 2H).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred for 24 h
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-5f6fc9da31b548a98380b8a28a11bc9a
Source dataset
uspto-grants-2003_03
Patent number
US06531485B2

Reaction notes

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