Methanol → HCID 69590032, compound

HRID 857199Notes

Reaction equation

HRID 857199 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH:12]([C:18](OCC)=[O:19])[C:13](OCC)=[O:14].[BH4-].[Na+].CO.[Cl-].[Li+]>O1CCCC1>[OH:19][CH2:18][CH:12]([CH2:11]/[CH:10]=[CH:9]\[CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:13][OH:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 433294Lithium ChlorideHCID 4311764Sodium borohydride2×HCID 86589159HCID 86589159, compound

Product 1

HCID 69590032HCID 69590032, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl [4-(tetrahydro-2H-pyran-2-yloxy)-(Z)-2-butenyl]malonate (65.5 g) was dissolved in 650 ml of dry tetrahydrofuran, and 15.1 g of sodium borohydride was added thereto. A solution of 110 g of methanol/275 ml of tetrahydrofuran was added dropwise gradually with stirring under heating to reflux. Then, 13.18 g of lithium chloride and 11 g of sodium borohydride were added and refluxed for 1.5 hours. The reaction solution was cooled and poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform) to provide 22.8 g of the objective compound as oil.

Workup

  1. temperatureunder heating to reflux
  2. temperaturerefluxed for 1.5 hours
  3. temperatureThe reaction solution was cooled
  4. additionpoured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform)

Sources & evidence

ORD record
ord-7f7fb0724a6c47589cffa52252fccf0f
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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