Methanol → (3,3-Dimethoxy-1-vinylcyclobutyl)methanol

HRID 594873Notes

Reaction equation

HRID 594873 reaction equation
[CH3:1][O:2][C:3]1([O:13][CH3:14])[CH2:6][C:5]([CH:11]=[CH2:12])([C:7](OC)=[O:8])[CH2:4]1.CC(C[AlH]CC(C)C)C.CO>C1COCC1>[CH3:14][O:13][C:3]1([O:2][CH3:1])[CH2:4][C:5]([CH2:7][OH:8])([CH:11]=[CH2:12])[CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 86724271Methyl 3,3-dimethoxy-1-vinylcyclobutanecarboxylate

Product 1

HCID 86724270(3,3-Dimethoxy-1-vinylcyclobutyl)methanolYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3,3-dimethoxy-1-vinylcyclobutanecarboxylate (2.02 g, 10.09 mmol) in THF (20 mL) was added DIBAL-H (1.04M in toluene, 29 mL, 30.16 mmol) at 0° C. under argon, and the mixture was stirred for 30 minutes at 0° C. To the mixture was carefully added MeOH (29 mL) and Na2SO4.10H2O (29 g), and the mixture was stirred overnight. The mixture was filtered and evaporated under reduced pressure. And the residue was diluted with hexane/EtOAc=1:1 and filtrated through the pad of silica gel and concentrated in vacuo to give (3,3-dimethoxy-1-vinylcyclobutyl)methanol (1.42 g).

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationThe mixture was filtered
  3. customevaporated under reduced pressure
  4. additionAnd the residue was diluted with hexane/EtOAc=1:1
  5. filtrationfiltrated through the pad of silica gel
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3de55fefbf3b4cda953173b8834f245d
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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