HCID 13470486, compound → HCID 13470488, compound

HRID 462386Notes

Reaction equation

HRID 462386 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][Cl:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[Si:1]([O:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][Cl:15])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 13470486HCID 13470486, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13470488HCID 13470488, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

5.2 g of 6-chlorohex-3-yn-1-ol t-butyldimethylsilyl ether in 50 ml of ethanol was hydrogenated under 1 atmosphere of hydrogen in the presence of 0.3 g of Lindlar catalyst wntil 370 ml of hydrogen had been absorbed. The catalyst was removed by filtration thru celite and the ethanol evaporated in vacuo. The crude product was chromatographed on 200 g of silica gel, eluting with 1 to 4% ether/hexane. Distillation of the appropriate fractions gave 3.7 g of 6-chlorohex-3Z-en-1-ol t-butyldimethylsilyl ether, bp 80°/0.5 mm.

Workup

  1. customhad been absorbed
  2. customThe catalyst was removed by filtration thru celite
  3. customthe ethanol evaporated in vacuo
  4. customThe crude product was chromatographed on 200 g of silica gel
  5. washeluting with 1 to 4% ether/hexane
  6. distillationDistillation of the appropriate fractions

Sources & evidence

ORD record
ord-767356bb90b34274aa07f8549b419f8e
Source dataset
uspto-grants-1985_05
Patent number
US04515727

Reaction notes

Loading…