Pyridine → HCID 53882006, compound

HRID 2107801Notes

Reaction equation

HRID 2107801 reaction equation
N1C=CC=CC=1.[S:7]1[CH2:11][CH2:10][S:9][CH:8]1[CH2:12][C@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[CH2:19][OH:20].[C:21](Cl)(=[O:23])[CH3:22]>ClCCl>[C:21]([O:20][CH2:19][C@@H:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C@@H:13]1[CH2:12][CH:8]1[S:9][CH2:10][CH2:11][S:7]1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 54432968HCID 54432968, compound

Product 1

HCID 53882006HCID 53882006, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 290 μL (3.5 mmol) of pyridine was added to 0.740 g (3.18 mmol) of rac-cis-2-(1,3-dithiolan-2-yl methyl)cyclohexanemethanol in 5 mL of dichloromethane, followed by dropwise addition of 235 μL (3.5 mmol) of acetyl chloride. After 15 min at 0° C. and 30 min at 20° C., the reaction mixture was partitioned between water and dichloromethane and the organic solution washed with 1.0N HCl and with 5% KHCO3 solutions, dried (MgSO4) and concentrated under vacuum to 865 mg (98%) of racemic cis-2-(1,3-dithiolan-2-yl methyl)cyclohexanemethanol acetate. TLC Rf 0.48 (SiO2, dichloromethane, I2 -brown).

Workup

  1. custom30 min at 20° C., the reaction mixture was partitioned between water and dichloromethane
  2. washthe organic solution washed with 1.0N HCl and with 5% KHCO3 solutions
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum to 865 mg (98%) of racemic cis-2-(1,3-dithiolan-2-yl methyl)cyclohexanemethanol acetate

Sources & evidence

ORD record
ord-541a7af94d7649c09c90356b528e7820
Source dataset
uspto-grants-1990_06
Patent number
US04935509

Reaction notes

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