HCID 86737367, compound → HCID 86737369, compound

HRID 1732839Notes

Reaction equation

HRID 1732839 reaction equation
[CH3:1][Li].[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13]2([O:20][CH2:19][CH2:18][O:17]2)[C:12]1([CH3:26])[CH2:21][CH2:22][CH2:23][CH:24]=[O:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CCOCC>[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13]2([O:17][CH2:18][CH2:19][O:20]2)[C:12]1([CH3:26])[CH2:21][CH2:22][CH2:23][CH:24]([OH:25])[CH3:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 86737367HCID 86737367, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 86737369HCID 86737369, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyllithium (63.3 ml, 0.0918 mol, 1.45 M in ether) is added dropwise to a solution of the aldehyde (2S*, 3R*)-3-benzyloxy-1,1-ethylenedioxy-2-methyl-2-(4'-oxobutyl)-cyclohexane (25.4 g, 0.0765 mol) in ether (1000 ml) at 0° C. in a nitrogen atmosphere. The cooling bath is removed and the mixture is stirred for 0.5 hours at ambient temperature. The mixture is then poured into a cold saturated sodium chloride solution (500 ml). The ether phase is separated and the aqueous phase is extracted with ether (3×100 ml). The ether phases are combined, dried (MgSO4) and the solvent is removed at reduced pressure. The crude product (27.1 g) is chromatographed on SilicAR CC-7 (300 g, Millinckrodt) in hexane. Elution with 10% ethyl acetate/hexane gives (2S*, 3R*)-3-benzyloxy-1,1-ethylenedioxy-2-methyl-2-(4'-hydroxypentyl)-cyclohexane as a colorless oil (25.8 g, 97%).

Workup

  1. customThe cooling bath is removed
  2. additionThe mixture is then poured into a cold saturated sodium chloride solution (500 ml)
  3. customThe ether phase is separated
  4. extractionthe aqueous phase is extracted with ether (3×100 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent is removed at reduced pressure
  7. customThe crude product (27.1 g) is chromatographed on SilicAR CC-7 (300 g, Millinckrodt) in hexane
  8. washElution with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0da47d08075a4e64a2d3e79c9ae46894
Source dataset
uspto-grants-1980_12
Patent number
US04239689

Reaction notes

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