Sodium Hydroxide → 3-Methoxypentane-1,5-diol

HRID 472972

Reaction equation

HRID 472972 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][CH:9]([CH2:15][C:16](OC)=[O:17])[CH2:10][C:11](OC)=[O:12].[OH-].[Na+]>C1COCC1>[CH3:7][O:8][CH:9]([CH2:15][CH2:16][OH:17])[CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14670803Dimethyl 3-methoxypentanedioateHCID 21226445Aluminium lithium hydride

Product 1

HCID 221012183-Methoxypentane-1,5-diolYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of LAH (1.77 g, 46.6 mmol) in THF (40 mL) under N2 was cooled to 0° C. and was added dimethyl 3-methoxypentanedioate (3.7 g, 19.5 mmol). The mixture was stirred overnight. Aqueous NaOH (1 N, 12 mL) was added at 0° C. The mixture was filtered and the cake was washed with EtOAc 3 times. The filtrate was dried and concentrated to give 3-methoxypentane-1,5-diol (1 g, 38%). 1H-NMR (CDCl3): 1.75 (m, 4H), 2.62 (s, 2H), 3.37 (m, 3H), 3.6 (m, 2H), 3.7 (m, 4H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe cake was washed with EtOAc 3 times
  3. customThe filtrate was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f455e93bea5b44a2b9cb778ebec09add
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Linked notes

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