2-(Di-tert-butylphosphino)biphenyl → 2-Ethoxy-4-p-tolyl-6-chloropropyl-1,2-oxaphosphorin 2-oxide

HRID 1499002Notes

Reaction equation

HRID 1499002 reaction equation
CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.[C:22]1([CH3:42])[CH:27]=[CH:26][C:25]([C:28]#[C:29][P:30](=[O:41])([O:34][C:35]([CH2:37][CH2:38][CH2:39][Cl:40])=[CH2:36])[O:31][CH2:32][CH3:33])=[CH:24][CH:23]=1>[Au].ClC(Cl)C>[CH2:32]([O:31][P:30]1(=[O:41])[CH:29]=[C:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:42])=[CH:23][CH:24]=2)[CH:36]=[C:35]([CH2:37][CH2:38][CH2:39][Cl:40])[O:34]1)[CH3:33]

Participants

5

Reactant 2

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 90019180Ethyl 5-chloropent-1-en-2-yl p-tolylethynylphosphonate

Product 1

HCID 715466022-Ethoxy-4-p-tolyl-6-chloropropyl-1,2-oxaphosphorin 2-oxideYield 78%

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 63651,1-DichloroethaneSolvent2×

Procedure

Method 1—A gold (Ag(I)) catalyst {[Au(JohnPhos)NCCH3]+SbF6—} [JohnPhos:(2-biphenyl)di-tent-butylphosphine] (11.3 mg, 0.015 mmol) was put into a reaction container, and dichloroethane (0.4 mL) was put thereinto. After stirring at room temperature for 5 minutes, ethyl 5-chloropent-1-en-2-yl p-tolylethynylphosphonate (Example 9, 97.8 mg, 0.3 mmol) diluted with 0.5 mL of dichloroethane was added thereto, and when all of the starting materials disappeared in the TLC, the reaction was allowed to be completed. After the solvent was removed under low atmospheric pressure, the product was separated by chromatography to obtain 2-ethoxy-4-p-tolyl-6-chloropropyl-1,2-oxaphosphorin 2-oxide (76.3 mg, 78%) which is a title compound.

Workup

  1. additionwas added
  2. customAfter the solvent was removed under low atmospheric pressure
  3. customthe product was separated by chromatography

Sources & evidence

ORD record
ord-6227305c3c6b49038bd325e6bacc1f9f
Source dataset
uspto-grants-2015_12
Patent number
US09200019B2

Reaction notes

Loading…