Dichloromethane → HCID 66939648, compound

HRID 1364177Notes

Reaction equation

HRID 1364177 reaction equation
[CH2:1]([O:8][C:9](=[O:12])[CH:10]=[CH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:20][CH:21]([SH:23])[CH3:22].ClCCl>C(O)C.O>[CH2:1]([O:8][C:9](=[O:12])[CH2:10][CH2:11][S:23][CH:21]([CH3:22])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 63642-PropanethiolHCID 8471TriethylamineHCID 75617Benzyl acrylate

Product 1

HCID 66939648HCID 66939648, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To benzylacrylate (100 mg, 0.617 mmol) in ethanol (2 mL) are added triethylamine (95 uL, 0.679 mmol) and 2-propanethiol (58 uL, 0.617 mmol). After stirring at rt during 2 h, the solvent is evaporated to give a residue which is treated with dichloromethane and water. The organic phase is dried and evaporated to afford a colorless oil before purification by preparative HPLC (Column Waters C18 ODB 5 μm 19×50, Gradient: 0-2.5 min 5% ACN, 2.5-12.5 min 5-100% ACN, 12.5-15 min 100% ACN) to yield the title compound.

Workup

  1. customthe solvent is evaporated
  2. customto give a residue which
  3. customThe organic phase is dried
  4. customevaporated
  5. customto afford a colorless oil
  6. custombefore purification by preparative HPLC (Column Waters C18 ODB 5 μm 19×50, Gradient: 0-2.5 min 5% ACN, 2.5-12.5 min 5-100% ACN, 12.5-15 min 100% ACN)

Sources & evidence

ORD record
ord-ae446e5479e5477f861068a05ac2ee91
Source dataset
uspto-grants-2011_02
Patent number
US07888351B2

Reaction notes

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