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

HRID 1427760Notes

Reaction equation

HRID 1427760 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-750f22141cdf4521bf4a7431ced0e5c4
Source dataset
uspto-grants-2015_01
Patent number
US08933015B2

Reaction notes

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