Hydrochloric Acid → HCID 13534072, compound

HRID 651931Notes

Reaction equation

HRID 651931 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][C:13]12[O:20][C:17]([CH3:21])([CH:18]=[CH:19]1)[CH2:16][CH:15]([OH:22])[CH2:14]2.Cl>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:22][CH:15]2[CH2:16][C:17]3([CH3:21])[O:20][C:13]([CH3:12])([CH:19]=[CH:18]3)[CH2:14]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 13534071HCID 13534071, compound

Product 1

HCID 13534072HCID 13534072, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

para-Toluenesulfonyl chloride (15.5 g, ) was added portionwise over 20 minutes to an ice-cold stirred solution of 1,5-dimethyl-8oxabicyclo[3.2.1]oct-6-en-3-ol (10.0 g, ) in dry pyridine (75 ml). The reaction mixture was stirred at 0° C. for 0.5 hour, allowed to stand in a refrigerator (0° C.) for 72 hours, and poured into a mixture of 80 ml concentrated hydrochloric acid and 100 g of ice. After stirring for 10 minutes, the precipitated solid was filtered. The collected solid dissolved methylene chloride was dried (MgSO4), filtered and concentrated to give 17.6 g (88%) of the desired product, m.p. 75°-77° C., as a 70:30 mixture of epimers.

Workup

  1. waitto stand in a refrigerator (0° C.) for 72 hours
  2. stirringAfter stirring for 10 minutes
  3. filtrationthe precipitated solid was filtered
  4. dissolutionThe collected solid dissolved methylene chloride
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d33eada2d14f4ee39c17ec46ec5643d1
Source dataset
uspto-grants-1987_06
Patent number
US04670041

Reaction notes

Loading…