Ethanethiol → HCID 20205312, compound

HRID 2166550Notes

Reaction equation

HRID 2166550 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][CH2:17][N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[CH2:23]([SH:25])[CH3:24]>B(F)(F)F.CCOCC>[CH2:23]([S:25][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1)[CH2:16][CH2:17][N:18]1[CH:22]=[CH:21][CH:20]=[N:19]1)[CH3:24]

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 53841824HCID 53841824, compound

Product 1

HCID 20205312HCID 20205312, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Conditions

Temperature
25 °C

Procedure

4.51 g of 1-benzyloxy-4-[3-(1-pyrazolyl)prop-1-enyl]benzene were dissolved in a mixture of 25 ml of ethanethiol and 25 ml of boron trifluoride diethyl etherate, and the resulting mixture was stirred at 25° C. for 0.75 hours. The excess thiol was removed by evaporation, and the residue was partitioned between ethyl acetate and water. The organic phase was separated, dried over sodium sulfate, and filtered. The filtrate was evaporated, and the residue was chromatographed on silica gel using chloroform for the elution. The eluate was evaporated, whereby 3.5 g (86%) of 4-[1-ethylthio-3-(1-pyrazolyl)propyl]phenol in the form of an oil was obtained.

Workup

  1. customThe excess thiol was removed by evaporation
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customthe residue was chromatographed on silica gel
  8. washfor the elution
  9. customThe eluate was evaporated

Sources & evidence

ORD record
ord-83cddea315a243ccbc9dcfc1ac7e5969
Source dataset
uspto-grants-1983_06
Patent number
US04387100

Reaction notes

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