Methyl chloroformate → HCID 54465876, compound

HRID 2225743Notes

Reaction equation

HRID 2225743 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:25])[C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.Cl[C:27](OC)=O>ClCCl.C(N(CC)CC)C.O>[CH3:27][O:23][C:22](=[O:24])[C:21](=[O:25])[C:18]1[CH:19]=[CH:20][C:15]([S:14][CH2:13][CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 6586Methyl chloroformateHCID 19004335HCID 19004335, compound

Product 1

HCID 54465876HCID 54465876, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of crude 4-[[2-(2-naphthalenyloxy)ethyl]thio]-alpha-oxobenzeneacetic acid (1.6 g) in dichloromethane (500 mL) and triethylamine (1 mL) was treated with methyl chloroformate (0.58 mL) and stirred at room temperature for 1 hour. The mixture was diluted with water, extracted with dichloromethane, dried (Na2SO4), filtered and evaporated. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 2:1) and crystallized from dichloromethane-diethyl ether to provide 0.85 g of 4-[[2-(2-naphthalenyloxy)ethyl]thio]-alpha-oxobenzeneacetic acid methyl ester, mp 124°-125° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. extractionThe material from dichloromethane extraction
  6. customwas purified by HPLC (dichloromethane-hexane; 2:1)
  7. customcrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-63522d316c2244fa93e6334a4cac97fe
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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