2-Methyl-2-butene → HCID 69232261, compound

HRID 1181103Notes

Reaction equation

HRID 1181103 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH:23]=[O:24])([CH3:4])([CH3:3])[CH3:2].CC(=CC)C.[O-:31]Cl=O.[Na+]>C(O)(C)(C)C.O>[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]=[CH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:25])=[C:10]([CH:11]=1)[C:23]([OH:31])=[O:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 724795793-(4-Benzyloxy-2-formyl-phenyl)-acrylic acid tert-butyl ester

Product 1

HCID 69232261HCID 69232261, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(4-benzyloxy-2-formyl-phenyl)-acrylic acid tert-butyl ester (6.70 g, 19.8 mmol) in tert-butanol (150 mL) was treated with 2-methyl-2-butene (50 mL) and cooled to 0° C. A solution of NaClO2 (17.0 g, 188 mmol) and NaH2PO4 (17.0 g, 142 mmol) in H2O (200 mL) was added, and the mixture was stirred at 0° C. for 15 min. The ice bath was removed, and the mixture was stirred at room temperature for 2 h. The organic layer was separated, and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified using silica gel chromatography (hexanes/EtOAc 9/1 to 0/10) to afford the title compound as white solid (6.78 g, 96%). 1H NMR (400 MHz, CDCl3): δ 1.52 (s, 9H), 5.12 (s, 2H), 6.20 (d, 1H, J=16.2 Hz), 7.13 (dd, 1H, J=3.6, 9.0 Hz), 7.34-7.45 (m, 5H), 7.58 (d, 1H, J=8.8 Hz), 7.64 (d, 1H, J=2.4 Hz), 8.41 (d, 1H, J=16.2 Hz).

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at room temperature for 2 h
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-ec366cca258846c5833141d48836c71f
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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