Water → HCID 22880248, compound

HRID 367366Notes

Reaction equation

HRID 367366 reaction equation
C([C@@H]1[O:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)(O)[C@@:7]([CH2:20][CH3:21])([CH3:19])[O:6]1)(C)(C)C.[OH2:22].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH2:34]>>[OH:6][C@:7]([CH3:19])([CH2:20][CH3:21])[C:8]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:18])(=[O:34])=[O:22])=[CH:13][CH:12]=1)=[O:9]

Participants

4

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 57227238HCID 57227238, compound

Product 1

HCID 22880248HCID 22880248, compound

Procedure

A mixture of the dioxolanol from Step 3 (46.2 g) in water (50 mL) with p-toluenesulfonic acid mono hydrate (1.3 g) was refluxed for 1 hour. The reaction was allowed to cool to r.t. and extract twice with EtOAc (200+150 mL). To this solution was added t-BuOH (175 mL) and Aliquat® 336. This solution was cooled to 10° C. and then a solution of OXONE® (130 g) in water (800 mL) was added over 30 min. The resulting mixture was stirred at r.t. for 20 h. The reaction mixture was neutralized by carefull and portionwise addition of aqueous saturated NaHCO3 and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give a yellow syrup. 1H NMR(CD3COCD3): δ0.90 (3H, t), 1.49 (3H, s), 1.81 (1 H, m), 1.95 (1H, s, OH), 1.99 (1H, m), 3.17 (3H, s), 8.02 (2H, d), 8.32 (2H, d).

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionextract twice with EtOAc (200+150 mL)
  3. additionTo this solution was added t-BuOH (175 mL) and Aliquat® 336
  4. temperatureThis solution was cooled to 10° C.
  5. additiona solution of OXONE® (130 g) in water (800 mL) was added over 30 min
  6. additionportionwise addition of aqueous saturated NaHCO3
  7. extractionextracted with EtOAc
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated
  10. customto give a yellow syrup

Sources & evidence

ORD record
ord-1ca03c5d24cc4899bcc5a21fcdd26100
Source dataset
uspto-grants-2000_10
Patent number
US06133292

Reaction notes

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