Benzyl mercaptan → HCID 86743023, compound

HRID 1761968Notes

Reaction equation

HRID 1761968 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[F:14][C:15]1[CH:22]=[CH:21][C:18](C=O)=[CH:17][CH:16]=1.C1C[O:26][CH2:25]C1>>[F:14][C:15]1[CH:22]=[CH:21][C:18]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH:1]([SH:8])[CH2:25][OH:26])=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 7509Benzyl mercaptanHCID 8028Tetrahydrofuran2×HCID 680234-FluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 86743023HCID 86743023, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 12.4 g (0.1 mole) of benzyl mercaptan (ie, benzenemethanethiol) in 150 ml of THF at 0° C. under moisture-free conditions, was added, dropwise, 14 g (0.22 mole) of n-butyllithium (1.6 m in hexane). After stirring at 0° C. for 4 hours (orange precipitate forms), the mixture was cooled to -25°. To this mixture was added a solution of 12.4 g (0.1 mole) of p-fluorobenzaldehyde in 100 ml of THF, dropwise. After stirring at -25° C. for 1 hour, a yellow solution occurs. The reaction was quenched with saturated aqueous ammonium chloride and the organic material was extracted once with MTBE and then once with methylene chloride. The organic solutions were combined and dried, and the solvent was removed under reduced pressure to give 25 g of the title product of this step as an oil (80:20 mixture of isomers), which was used in the next step without any further purification.

Workup

  1. temperaturethe mixture was cooled to -25°
  2. stirringAfter stirring at -25° C. for 1 hour
  3. customThe reaction was quenched with saturated aqueous ammonium chloride
  4. extractionthe organic material was extracted once with MTBE
  5. customdried
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2215d079f0804cf8a491e31fa8faf874
Source dataset
uspto-grants-1989_05
Patent number
US04829081

Reaction notes

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