Hydrochloric Acid → HCID 131721740, compound

HRID 1637791Notes

Reaction equation

HRID 1637791 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[C@H:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(OCC)(=O)C.Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:19]3[CH:20]=[CH:21][C:22]([O:25][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:23][CH:24]=3)[C@H:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 57180828HCID 57180828, compound

Product 1

HCID 131721740HCID 131721740, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(+,-) cis 7-methoxy-4-(4-hydroxy-phenyl)-3-phenyl-chroman (7.5 g, 22.6 mmol) was dissolved in pyridine (35 ml), and methanesulfonylchloride (3.85 ml, 49.6 mmol) was added dropwise in 5 min. The reaction mixture was refluxed for 30 min, cooled to room temperature, and ethyl acetate (100 ml) was added. The reaction mixture was acidified with 6N Hydrochloric acid (100 ml), and the separated aqueous phase extracted with ethyl acetate (25 ml). The combined organic extracts were washed with 1N hydrochloric acid (50 ml), water (2×50 ml), dried with magnesium sulphate and evaporated to give a slightly yellow solid, which was recrystallised from ethanol, and vacuum dried.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. extractionthe separated aqueous phase extracted with ethyl acetate (25 ml)
  3. washThe combined organic extracts were washed with 1N hydrochloric acid (50 ml), water (2×50 ml)
  4. dry with materialdried with magnesium sulphate
  5. customevaporated
  6. customto give a slightly yellow solid, which
  7. customwas recrystallised from ethanol, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-6606aef87007465faecc6efe24d15906
Source dataset
uspto-grants-2000_03
Patent number
US06043269

Reaction notes

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