Sodium Sulfite → HCID 68706209, compound

HRID 2118384Notes

Reaction equation

HRID 2118384 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:17][C:16]3[C:11](=[CH:12][C:13]([OH:18])=[CH:14][CH:15]=3)[C@@H:10]3[CH2:19][S:20][CH2:21][C@H:9]23)=[CH:4][CH:3]=1.[OH:22]OS([O-])=O.[K+].[O-]S([O-])=O.[Na+].[Na+]>CO.O.CCOC(C)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[O:17][C:16]3[C:11](=[CH:12][C:13]([OH:18])=[CH:14][CH:15]=3)[C@@H:10]3[CH2:19][S@@:20](=[O:22])[CH2:21][C@H:9]23)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 11347117HCID 11347117, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 68706209HCID 68706209, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of enantiomer A of 4-(4-hydroxy-phenyl)-1,3a,4,9b-tetrahydro-3H-5-oxa-2-thia-cyclopenta[a]naphthalen-8-ol 11d (20 mg, 0.066 mmol) in MeOH/H2O (1:1, 3 mL) add oxone (40 mg, 0.066 mmol). Stir the reaction at room temperature for 30 minutes. Add 1.0 M Na2SO3 and stir the reaction for 5 minutes. Dilute with EtOAc and wash with saturated sodium bicarbonate. Extract aqueous layer with EtOAc (2×). Combine organic extracts, dry (Na2SO4), filter and concentrate to afford 4-(4-hydroxy-phenyl)-2-oxo-1,2,3,3a,4,9b-hexahydro-5-oxa-2λ4-thia-cyclopenta[a]naphthalen-8-ol 13 (17 mg, 0.054 mmol, 85%). 1H NMR (δ, 400 MHz, MeOD) 7.44 (d, 2H, J=8.8 Hz), 6.85 (d, 2H, J=8.8 Hz), 6.75 (d, 1H, J=8.8 Hz), 6.70 (d, 1H, J=2.8 Hz), 6.61 (dd, 1H, J=8.8, 2.8 Hz), 5.19 (s, 1H), 4.19 (dd, 1H, J=6.2, 6.2 Hz), 3.76 (d, 1H, J=7.9 Hz), 3.06-2.94 (m, 1H), 2.84 (dd, 1H, J=14.1, 5.3 Hz), 2.62 (dd, 1H, J=13.0, 5.5 Hz), 2.29 (dt, 1H, J=5.2, 14.0 Hz). HPLC (Zorbax C18 column; 10 to 100% CH3CN/H2O for 10 min then 100% CH3CN for 5 min; 1 mL/min; tr 7.17 min). LRMS calcd for C17H15O4S: 315.1; found (ES−, M−H): 315.2.

Workup

  1. customthe reaction at room temperature for 30 minutes
  2. stirringstir
  3. customthe reaction for 5 minutes
  4. washwash with saturated sodium bicarbonate
  5. dry with materialCombine organic extracts, dry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-7b05fe0b4d5440b18d91f296b1b5f56a
Source dataset
uspto-grants-2008_10
Patent number
US07442812B2

Reaction notes

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