Water → 3-Dihydropyranyloxy-3-methyl butanol

HRID 374394Notes

Reaction equation

HRID 374394 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH:8]1[O:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16](OC)=[O:17].O.[OH-].[Na+]>C(OCC)C.O1CCCC1>[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH:8]1[O:13][C:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][OH:17]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86749184Methyl beta-dihydropyranyloxyisovalerate

Product 1

HCID 677330413-Dihydropyranyloxy-3-methyl butanolYield 76.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Thereafter, 0.7 g of lithium aluminum hydride was suspended in 20 ml of diethyl ether, and a solution of 1.98 g of methyl β-dihydropyranyloxyisovalerate in 3 ml of diethyl ether was slowly dropwise added to the suspension, and a reaction was allowed to proceed at room temperature overnight. The mixture was further heated and refluxed for 1 hr and then cooled, and 0.7 ml of water, 0.7 ml of a 15% aqueous sodium hydroxide solution and 2.1 ml of water were successively added in that order with ice cooling. The mixture was stirred at room temperature for 1 hr, 20 ml of tetrahydrofuran was added thereto, and the mixture was stirred for additional one hr. The precipitat was collected by filtration and washed with 10 ml of tetrahydrofuran, and the washing was combined with the filtrate. The solvent was removed from the combined filtrate and washing by distillation under a reduced pressure to obtain 1.32 g of crude 3-dihydropyranyloxy-3-methyl butanol.

Workup

  1. temperatureThe mixture was further heated
  2. temperaturerefluxed for 1 hr
  3. temperaturecooled
  4. stirringthe mixture was stirred for additional one hr
  5. customThe precipitat
  6. filtrationwas collected by filtration
  7. washwashed with 10 ml of tetrahydrofuran
  8. customThe solvent was removed from the combined filtrate
  9. washwashing by distillation under a reduced pressure

Sources & evidence

ORD record
ord-657b72b2d2454ca09ddeda17bccb981e
Source dataset
uspto-grants-1996_01
Patent number
US05480580

Reaction notes

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