Boron trifluoride etherate → HCID 86753937, compound

HRID 1418806Notes

Reaction equation

HRID 1418806 reaction equation
[CH3:1][C:2]1[C:7]2[C:8](=O)[CH2:9][CH2:10][S:11](=[O:13])(=[O:12])[C:6]=2[C:5]([CH3:15])=[CH:4][C:3]=1[C:16]([OH:18])=[O:17].[CH2:19]([SH:22])[CH2:20][SH:21].B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:1][C:2]1[C:7]2[C:8]3([CH2:9][CH2:10][S:11](=[O:13])(=[O:12])[C:6]=2[C:5]([CH3:15])=[CH:4][C:3]=1[C:16]([OH:18])=[O:17])[S:22][CH2:19][CH2:20][S:21]3

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 54393632HCID 54393632, compound

Product 1

HCID 86753937HCID 86753937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.60 g of 3,4-dihydro-5,8-dimethyl4-oxo-2H-1-benzothiopyran-6-carboxylic acid 1,1-dioxide in 30 mL of methylene chloride was added 0.24 mL of 1,2-ethanedithiol (purchased from Aldrich Chemical Co.) and 0.35 mL of boron trifluoride diethyl etherate (purchased from Janssen Chimica). The mixture was refluxed overnight and then concentrated under reduced pressure to dryness. To the resulting residue was added 10 mL of dilute hydrochloric acid of pH 1. The mixture was extracted with ethyl acetate, and the combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure to afford 0.62 g of the title compound of Step A as an orange solid which had a melting point >250° C. 1H NMR ((CD3)2SO): δ 2.65 (s, 3H), 2.77 (s, 3H), 2.94 (m, 2H), 3.55-3.80 (m, 6H), 7.50 (s, 1H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationconcentrated under reduced pressure to dryness
  3. additionTo the resulting residue was added 10 mL of dilute hydrochloric acid of pH 1
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c8d4adbc92548c7831c9eed2a4ecb85
Source dataset
uspto-grants-1999_03
Patent number
US05885936

Reaction notes

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