Water → [1-(Hydroxymethyl)-3,3-dimethoxycyclobutyl]methanol

HRID 1966160Notes

Reaction equation

HRID 1966160 reaction equation
[CH3:1][O:2][C:3]1([O:19][CH3:20])[CH2:6][C:5]([C:13](OC(C)C)=[O:14])([C:7](OC(C)C)=[O:8])[CH2:4]1.[AlH4-].[Li+].O.[OH-].[Na+]>C1COCC1>[CH3:20][O:19][C:3]1([O:2][CH3:1])[CH2:4][C:5]([CH2:7][OH:8])([CH2:13][OH:14])[CH2:6]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 49133591,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylate

Product 1

HCID 14862499[1-(Hydroxymethyl)-3,3-dimethoxycyclobutyl]methanolYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., to a solution of diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate (3.0 g, 0.010 mol) in THF (20 mL) was added 2.0 M of lithium tetrahydroaluminate in tetrahydrofuran (16 mL) slowly with stirring. The mixture was stirred for 2 h, allowing warm up to rt. At 0° C., to the reaction was added dropwise water (1.2 mL), 15% NaOH solution (1.2 mL) and water (3.6 mL) successively and the resultant mixture was stirred for 20 min at rt. The mixture was filtered and the filtrate was concentration to give the desired product (1.64 g, 89%) as colorless oil which was used directly in the next step without purification.

Workup

  1. stirringThe mixture was stirred for 2 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentration

Sources & evidence

ORD record
ord-ad55c247f44f4751b65ca3b37ee6c40e
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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