Methanol → HCID 54116443, compound

HRID 1195635Notes

Reaction equation

HRID 1195635 reaction equation
[CH3:1][C:2](=[CH2:12])[CH2:3][CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[BH4-].[Na+].[CH3:15][OH:16]>[OH-].[Na+].[Hg]>[CH3:15][O:16][C:2]([CH3:1])([CH3:12])[CH2:3][CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 122906552H-Pyran, tetrahydro-2-[(3-methyl-3-butenyl)oxy]-

Product 1

HCID 54116443HCID 54116443, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 14798Sodium HydroxideSolvent2×

Procedure

To 2-(3-methyl-3-butenyloxy)tetrahydropyran (150.0 g, 881.0 mmol) in methanol (600 ml) was added mercuric acetate (309 g, 969 mmol) and the mixture was stirred until it became homogeneous. To this solution was added 0.5N NaOH (500 ml) in one portion followed by dropwise addition of 0.5N NaBH4 in 0.5N NaOH (500 ml). The mixture is stirred until mercury metal congeals at the bottom of the flask. The solution is decanted into a separatory funnel and extracted with ether (3×300 ml). The combined ethereal extracts are dried (MgSO4) and concentrated to afford 166 g (93%) of 2-(3-methoxy-3-methylbutyloxy)tetrahydropyran as a colorless liquid.

Workup

  1. customThe solution is decanted into a separatory funnel
  2. extractionextracted with ether (3×300 ml)
  3. dry with materialThe combined ethereal extracts are dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0db9edb1f4f04f4ab51c23f8f722f250
Source dataset
uspto-grants-1992_05
Patent number
US05112595

Reaction notes

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