Methanol → HCID 21507654, compound

HRID 1287300Notes

Reaction equation

HRID 1287300 reaction equation
[O:1]=[C:2]1[O:7][CH:6]([CH2:8][CH2:9][CH2:10][C:11]2([CH3:18])[O:15][CH:14]([CH3:16])[CH:13]([CH3:17])[O:12]2)[CH2:5][CH2:4][CH2:3]1.[CH:19]([Mg]Cl)=[CH2:20].CO.[Cl-].[NH4+].O1CC[CH2:29][CH2:28]1>CCOCC>[OH:7][CH:6]([CH2:8][CH2:9][CH:10]([C:11]1([CH3:18])[O:15][CH:14]([CH3:16])[CH:13]([CH3:17])[O:12]1)[CH2:19][CH3:20])[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH:28]=[CH2:29]

Participants

7

Reactant 5

HCID 887MethanolHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 21507653HCID 21507653, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 21507654HCID 21507654, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution containing (±)-2-[3-(6-oxo-2-tetrahydropyranyl)propyl] -2,4,5-trimethyl-1,3-dioxolane (40 g.) in 200 ml. of tetrahydrofuran was cooled to -45° under nitrogen. A 2.12 molar solution of vinyl magnesium chloride in tetrahydrofuran was added dropwise at -45° to -50° over 10 minutes, stirring being continued at -55° to -60° for an additional 35 minutes. Then 10 ml. of methanol was added dropwise and the reaction mixture was poured onto a slurry of ice, ammonium chloride and ether. The ether layer was separated and the aqueous layer re-extracted twice with more ether. The ether layers were washed three times with brine, combined and dried over sodium sulfate. A small sample of the ether solution upon evaporation yielded 2-(7-hydroxy-3-oxo-dodec-1-en-10-yl)-2,4,5-trimethyl-1,3-dioxolane as an oil, UV absolute maximum (in ethanol) at 208 mμ,ε = 9,100.

Workup

  1. customThe ether layer was separated
  2. extractionthe aqueous layer re-extracted twice with more ether
  3. washThe ether layers were washed three times with brine
  4. dry with materialdried over sodium sulfate
  5. customA small sample of the ether solution upon evaporation

Sources & evidence

ORD record
ord-3fa21e14abd94eafbc5f2c17abbfa93f
Source dataset
uspto-grants-1976_10
Patent number
US03984427

Reaction notes

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