Sodium Methoxide → (E)-(2S,3S,4S,5S)-3,5-Dimethoxy-2,4-dimethyl-nona-6,8-dien-1-ol

HRID 1427753Notes

Reaction equation

HRID 1427753 reaction equation
C([O:5][CH2:6][C@H:7]([CH3:20])[C@H:8]([O:18][CH3:19])[C@@H:9]([CH3:17])[C@@H:10]([O:15][CH3:16])/[CH:11]=[CH:12]/[CH:13]=[CH2:14])(C)(C)C.C[O-].[Na+]>CO>[CH3:19][O:18][C@H:8]([C@@H:9]([CH3:17])[C@@H:10]([O:15][CH3:16])/[CH:11]=[CH:12]/[CH:13]=[CH2:14])[C@@H:7]([CH3:20])[CH2:6][OH:5]

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 86675853(E)-(5S,6S,7S,8S)-9-tert-Butoxy-5,7-dimethoxy-6,8-dimethyl-nona-1,3-diene

Product 1

HCID 86675852(E)-(2S,3S,4S,5S)-3,5-Dimethoxy-2,4-dimethyl-nona-6,8-dien-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (E)-(5S,6S,7S,8S)-9-tert-Butoxy-5,7-dimethoxy-6,8-dimethyl-nona-1,3-diene (1.3 g, 4.2 mmol) in anhydrous methanol (10 ml) at room temperature and under an atmosphere of nitrogen was added sodium methoxide (30% wt in MeOH, 3.7 ml, 20.8 mmol). The reaction was stirred overnight. A further amount of sodium methoxide (30% wt in MeOH, 3.7 ml, 20.8 mmol) was added and the reaction was stirred for a further 1 hour. The reaction was quenched with saturated ammonium chloride and extracted with dichloromethane (3×). The combined organic layers were dried by passing through a hydrophobic frit and concentrated in vacuo. The product was purified by flash chromatography (SiO2, iHex/EtOAc, 10:1 then 2:1) to afford 2.0 g (100%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 6.40 (dt, J=16.8 Hz, 10.4 Hz, 10.2 Hz, 1H), 6.23 (dd, J=15.2 Hz, 10.4 Hz, 1H), 5.46 (dd, J=15.2 Hz, 8.4 Hz, 1H), 5.26 (dd, J=17.0 Hz, 1.6 Hz, 1H), 5.14 (dd, J=10.2 Hz, 1.6 Hz, 1H), 3.77-3.53 (m, 3H), 3.51 (s, 3H), 3.42 (t, J=9.3 Hz, 1H), 3.27 (s, 3H), 2.75 (dd, J=8.4 Hz, 3.1 Hz, 1H), 1.91 (m, 1H), 1.72 (m, 1H), 0.85 (d, J=7.1 Hz, 3H), 0.80 (d, J=7.1 Hz, 3H).

Workup

  1. stirringthe reaction was stirred for a further 1 hour
  2. customThe reaction was quenched with saturated ammonium chloride
  3. extractionextracted with dichloromethane (3×)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography (SiO2, iHex/EtOAc, 10:1
  7. custom2:1) to afford 2.0 g (100%) as a clear oil

Sources & evidence

ORD record
ord-8562584ee76e4065a0648696b49258e4
Source dataset
uspto-grants-2015_01
Patent number
US08933015B2

Reaction notes

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