6,6-Ethylenedioxy-2-methyl-2-(4'-oxobutyl)-oxepane → 6,6-Ethylenedioxy-2-(4'-hydroxypentyl)-2-methyloxepane

HRID 851335Notes

Reaction equation

HRID 851335 reaction equation
[CH3:1][Li].[CH2:3]1[CH2:19][O:18][C:5]2([CH2:11][O:10][C:9]([CH3:17])([CH2:12][CH2:13][CH2:14][CH:15]=[O:16])[CH2:8][CH2:7][CH2:6]2)[O:4]1>CCOCC>[CH2:19]1[CH2:3][O:4][C:5]2([CH2:11][O:10][C:9]([CH2:12][CH2:13][CH2:14][CH:15]([OH:16])[CH3:1])([CH3:17])[CH2:8][CH2:7][CH2:6]2)[O:18]1

Participants

4

Reactant 2

HCID 131881866,6-Ethylenedioxy-2-methyl-2-(4'-oxobutyl)-oxepaneHCID 178418348HCID 178418348, compound

Product 1

HCID 131881876,6-Ethylenedioxy-2-(4'-hydroxypentyl)-2-methyloxepaneYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyllithium (10 ml, 0.0184 mol, 1.84 M in hexane) is added dropwise to a solution of 6,6-ethylenedioxy-2-methyl-2-(4'-oxobutyl)-oxepane (3.3 g) in ether (150 ml) at 0° C. in a nitrogen atmosphere. The cooling bath is removed and the mixture is stirred for 0.5 hour at ambient temperature. The mixture is poured into cold satd. NaCl (300 ml). The ether layer is separated and the aqueous layer extracted with ether (3×50 ml). The ether phases are combined, dried (MgSO4) and the solvent is removed at reduced pressure. The crude product (3.6 g) is chromatographed on SilicAR CC-7 (70 g) in hexane. Elution with 15% ethyl acetate/hexane gives 6,6-ethylenedioxy-2-(4'-hydroxypentyl)-2-methyloxepane (15) as a clear colorless oil (3.3 g, 94%).

Workup

  1. customThe cooling bath is removed
  2. additionThe mixture is poured into cold satd
  3. customThe ether layer is separated
  4. extractionthe aqueous layer extracted with ether (3×50 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent is removed at reduced pressure
  7. customThe crude product (3.6 g) is chromatographed on SilicAR CC-7 (70 g) in hexane
  8. washElution with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ba1b4ff20e2a44959f1af7d944a3c30c
Source dataset
uspto-grants-1983_05
Patent number
US04384126

Reaction notes

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