Acetic Acid → HCID 118184920, compound

HRID 2177397Notes

Reaction equation

HRID 2177397 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=O)[CH3:2].[CH2:18]([SH:21])[CH2:19][SH:20].B(F)(F)F.CCOCC.CC(O)=O>ClCCl>[OH:10][C:8]1[CH:7]=[CH:6][C:5]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:4]([C:1]2([CH3:2])[S:21][CH2:18][CH2:19][S:20]2)[CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 118184937HCID 118184937, compound

Product 1

HCID 118184920HCID 118184920, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100-mL round-bottom flask, was placed ethyl 3-(2-acetyl-4-hydroxyphenyl)propanoate (200 mg, 0.85 mmol, 1.00 equiv), dichloromethane (10 mL), ethane-1,2-dithiol (398 mg, 4.23 mmol, 5.00 equiv), BF3/Et2O (597 mg, 4.23 mmol, 5.00 equiv), AcOH (542 mg, 9.03 mmol, 8.00 equiv). The resulting solution was stirred for 2 h at 25° C. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The resulting mixture was concentrated under reduced pressure. The residue was applied to a silica gel column, eluting with ethyl acetate/petroleum ether (1:2). This resulted in 150 mg (57%) of ethyl 3-[4-hydroxy-2-(2-methyl-1,3-dithiolan-2-yl)phenyl]propanoate as light yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. washeluting with ethyl acetate/petroleum ether (1:2)
  4. customThis resulted in 150 mg (57%) of ethyl 3-[4-hydroxy-2-(2-methyl-1,3-dithiolan-2-yl)phenyl]propanoate as light yellow oil

Sources & evidence

ORD record
ord-ae7fb3a22ee040b2ad2c9f658363263d
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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