Hydrochloric Acid → HCID 54377319, compound

HRID 2227111Notes

Reaction equation

HRID 2227111 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH:3]=1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.Cl>N1C=CC=CC=1>[S:15]([O:8][CH:5]1[CH2:6][CH2:7][C:2]([CH3:1])=[CH:3][CH2:4]1)([C:12]1[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 12882493HCID 12882493, compound

Product 1

HCID 54377319HCID 54377319, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of alcohol 4C (R=methyl) (10 g) and p-toluenesulfonyl chloride (20.8 g) in anhydrous tetrahydrofaran (21 mL) at 0° C. is added anhydrous pyridine (21 mL). The reaction is allowed to stir in an ice bath for 2 hours, and is then allowed to stand at −20° C. for a further 16 hours. The reaction mixture is then poured into 2M HCl (75 mL) and extracted with ethyl acetate. The combined organic layers are extracted with brine and dried over sodium sulfate. The solvent is removed in vacuo.

Workup

  1. waitto stand at −20° C. for a further 16 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe combined organic layers are extracted with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-af340bcbabd44571b598eba2f270674c
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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