Methyl morpholine oxide → HCID 21884137, compound

HRID 722391Notes

Reaction equation

HRID 722391 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9](CC=C)[S:10]([C:13]2[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=2[F:23])(=[O:12])=[O:11])=[CH:5][CH:4]=1.C[N+]1([O-])CC[O:31]CC1.OS([O-])=O.[Na+].[CH3:40][C:41]([CH3:43])=[O:42].O>O=[Os](=O)(=O)=O>[OH:42][CH:41]([CH2:43][OH:31])[CH2:40][N:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[S:10]([C:13]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=1[F:23])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 21884091HCID 21884091, compoundHCID 23665763Sodium Bisulfite2×

Product 1

HCID 21884137HCID 21884137, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 4-methoxy-1-(N-(2-propenyl)pentafluorophenylsulfonamido)benzene (101 mg, 0.26 mmol) in acetone:water (8:1, 1 mL) at rt was added N-methylmorpholine N-oxide (34.0 mg, 0.29 mmol) and OsO4 (0.10 mL of 0.16 M solution in H2O, 1.60×10−2 mmol). After stirring at rt for 18 h, the reaction mixture was treated with saturated NaHSO3 (5 mL) and allowed to stir at rt. After 1 h, the reaction mixture was poured onto saturated NaHSO3 (5 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (1:1, 1:2/hexanes:EtOAc) afforded 90 mg (83%) of product as a white solid, mp 130–131° C. 1H NMR (CDCl3): d 7.11 (m, 2H), 6.85 (m, 2H), 3.78 (s, 3H), 3.90–3.65 (m, 5H). Anal. Calcd. for C16H13F5NO5S: C, 45.08; H, 3.07; N, 3.29; S, 7.52. Found: C, 45.09; H, 3.33; N, 3.27; S, 7.46.

Workup

  1. stirringto stir at rt
  2. waitAfter 1 h
  3. extractionextracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d054886795f24371afd95e1bb4cc4d2e
Source dataset
uspto-grants-2006_11
Patent number
US07138418B2

Reaction notes

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