Butyl vinyl ether → HCID 67107899, compound

HRID 2177729Notes

Reaction equation

HRID 2177729 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:61]([O:63]CCCC)=[CH2:62]>C(O)CO.C(Cl)Cl.Cl.[Pd](Cl)Cl>[C:61]([C:14]1[C:15]([O:22][CH3:23])=[C:16]([C:11]([CH2:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:12][CH:13]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:63])[CH3:62]

Participants

9

Reactant 4

HCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2×

Product 1

HCID 67107899HCID 67107899, compound

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 174Ethylene GlycolSolventHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.82 g), triethylamine (0.7 ml), 1,3-bis(diphenylphosphino)propane (0.04 g) and palladium chloride (0.01 g) in ethylene glycol (4 ml) was sealed in a vial under nitrogen and the mixture was stirred and heated to 140° C. Butyl vinyl ether (0.8 ml) was then added and the resultant mixture was stirred and heated at 140° C. for 2 hours. After cooling, the mixture was diluted with DCM and 1M hydrochloric acid was added. The mixture was stirred at room temperature for 30 minutes then the two layers were separated and the aqueous layer was extracted with further DCM. The combined organic layers were dried (MgSO4) and filtered. The filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-80%) to give crude ethyl 3-acetyl-6-(benzenesulphonylmethyl)-2-methoxybenzoate (0.33 g) as an oil.

Workup

  1. customwas sealed in a vial under nitrogen
  2. temperatureheated at 140° C. for 2 hours
  3. temperatureAfter cooling
  4. additionwas added
  5. stirringThe mixture was stirred at room temperature for 30 minutes
  6. customthe two layers were separated
  7. extractionthe aqueous layer was extracted with further DCM
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customThe residue was purified by chromatography on silica
  12. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-80%)

Sources & evidence

ORD record
ord-72ea1c04cd0147378bcf44e0589b5976
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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