2-Methyl-2-butene → HCID 66682626, compound

HRID 909543Notes

Reaction equation

HRID 909543 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([C:16]2[CH:21]=[C:20]([O:22][C@@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[CH:19]=[C:18]([O:28][C:29]3[CH:34]=[CH:33][C:32]([CH:35]=[O:36])=[CH:31][C:30]=3[F:37])[CH:17]=2)=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.P([O-])(O)(O)=[O:41].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>[Cl-].[Na+].O.O.C(O)(C)(C)C>[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([C:16]2[CH:17]=[C:18]([CH:19]=[C:20]([O:22][C@@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[CH:21]=2)[O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([OH:41])=[O:36])=[CH:31][C:30]=2[F:37])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 86649568HCID 86649568, compound

Product 1

HCID 66682626HCID 66682626, compoundYield 109.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Benzyl 5-{3-(2-Fluoro-4-formylphenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrole-2-carboxylate (6.33 g, 12.6 mmol) synthesized in Example (66d) was suspended in a mixed solvent of t-butanol (120 mL) and water (40 mL), and sodium dihydrogen phosphate dihydrate (8.86 g, 56.8 mmol) and 2-methyl-2-butene (12.05 mL, 113 mmol) were added. Under ice cooling, sodium chlorite (80%, 2.93 g, 25.9 mmol) was added slowly, and stirring was carried out at room temperature for 2 hours. Saturated brine (200 mL) was added, followed by extraction with dichloromethane (200 mL), and drying was carried out over anhydrous magnesium sulfate to afford the desired compound (7.17 g, yield ˜100%) as a pale yellow oil.

Workup

  1. additionwere added
  2. extractionfollowed by extraction with dichloromethane (200 mL)
  3. customdrying

Sources & evidence

ORD record
ord-ebf947cd9f184d4b9f39482801508e9e
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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