2-Methyl-2-butene → HCID 86675860, compound

HRID 1895770Notes

Reaction equation

HRID 1895770 reaction equation
[CH3:1][O:2][C@H:3]([C@@H:8]([CH3:27])[C@@H:9]([O:25][CH3:26])/[CH:10]=[CH:11]/[Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])[C@@H:4]([CH3:7])[CH:5]=[O:6].CC(=CC)C.Cl([O-])=[O:34].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O.[Cl-].[Na+].O>[CH3:1][O:2][C@H:3]([C@@H:8]([CH3:27])[C@@H:9]([O:25][CH3:26])/[CH:10]=[CH:11]/[Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])[C@@H:4]([CH3:7])[C:5]([OH:34])=[O:6]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86675858HCID 86675858, compound

Product 1

HCID 86675860HCID 86675860, compoundYield 90%

Reagents, catalysts & solvents 3

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

Procedure

To (E)-(2R,3R,4R,5R)-3,5-Dimethoxy-2,4-dimethyl-7-tributylstannanyl-hept-6-enal (98 mg, 0.2 mmol) in tert-butanol (2 ml) and 2-methyl-2-butene (0.22 ml, 2.03 mmol) at room temperature, was added a solution of sodium chlorite (92 mg, 1.02 mmol) and sodium dihydrogenphosphate (58 mg, 0.41 mmol) in water (0.5 ml). The reaction was stirred vigorously overnight, after which brine was added and then extracted with dichloromethane (2×). The organics were dried through a hydrophobic frit and concentrated in vacuo. The oily residue was left on a vacuum pump overnight to afford the product 5b as a solid (91 mg, 90%). 1H NMR (300 MHz, CDCl3) δ 6.05 (d, J=19.0 Hz, 1H), 5.58 (dd, J=19.0 Hz, 7.9 Hz, 1H), 3.72 (m, 1H), 3.38 (s, 3H), 3.23 (t, J=8.8 Hz, 1H), 3.16 (s, 3H), 2.52 (m, 1H), 1.61 (m, 1H), 1.43 (m, 6H), 1.24 (m, 6H), 1.01 (d, J=7.0 Hz, 3H), 0.82 (m, 15H), 0.71 (d, J=7.0 Hz, 3H).

Workup

  1. extractionextracted with dichloromethane (2×)
  2. customThe organics were dried through a hydrophobic frit
  3. concentrationconcentrated in vacuo
  4. waitThe oily residue was left on a vacuum pump overnight

Sources & evidence

ORD record
ord-f32c9b92b4cd4db4bc1a4d9d6feec0d4
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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