2-Methyl-2-butene → HCID 54400206, compound

HRID 726757Notes

Reaction equation

HRID 726757 reaction equation
[O-:1]Cl=O.[Na+].[CH:5]1([O:10][C:11]2[CH:12]=[C:13]([C@@H:19]([C:27]3[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=3)[CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH2:9][CH2:8][CH2:7][CH2:6]1.CC(=CC)C>O.CC(O)(C)C>[CH:5]1([O:10][C:11]2[CH:12]=[C:13]([C@@H:19]([C:27]3[CH:28]=[CH:29][C:30]([C:31]([OH:1])=[O:32])=[CH:33][CH:34]=3)[CH2:20][C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 53823624HCID 53823624, compound

Product 1

HCID 54400206HCID 54400206, compoundYield 101.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of NaClO2 (149 mg, 1.64 mmol) and NaH2PO4 ·H2O (227 mg, 1.64 mmol) in water (1 mL) was added to a solution of aldehyde from Step 3 (508 mg, 1.27 mmol) and 2-methyl-2-butene (0.94 mL, 8.9 mmol) in t-BuOH (6 mL). The reaction mixture was stirred at room temperature for 19 hours before 25% aqueous NH4OAc was added. The mixture was then extracted twice with EtOAc. The organic phase was washed with brine, dried (MgSO4) and evaporated to afford the title compound as a white solid (540 mg). 1H NMR (400 MHz, CDCl3): δ 1.55 (m, 2H), 1.75 (m, 6H), 3.35 (m, 2H), 3.80 (s, 3H), 4.20 (t, 1H), 4.60 (m, 1H), 6.60 (s, 1H), 6.65 (d, 1H), 6.75 (d, 1H), 7.00 (d, 2H), 7.25 (d, 2H), 8.00 (d, 2H), 8.45 (d, 2H).

Workup

  1. additionwas added
  2. extractionThe mixture was then extracted twice with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-9ae4b03785c84301b9ae228f4d9af41e
Source dataset
uspto-grants-1998_01
Patent number
US05710170

Reaction notes

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