Quinoline → rac. Z-1-benzyloxy-2-methyl-5-hepten-4-ol

HRID 427121Notes

Reaction equation

HRID 427121 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH:12]([OH:16])[C:13]#[C:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCCCCC>[CH2:1]([O:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH:12]([OH:16])/[CH:13]=[CH:14]\[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7047QuinolineHCID 12923299Rac. 1-benzyloxy-2-methyhept-5-yn-4-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12923294rac. Z-1-benzyloxy-2-methyl-5-hepten-4-ol

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8058HexaneSolvent

Procedure

A mixture of 1 g. (4.31 mmoles) of rac. 1-benzyloxy-2-methylhept-5-yn-4-ol, 0.1 g. of Lindlar catalyst, 0.04 ml. of quinoline and 30 ml. of hexane was stirred in an atmosphere of hydrogen, at room temperature, for 40 minutes during which time approximately one equivalent of hydrogen was taken up. The catalyst was filtered and washed with hexane then the combined filtrate and washes were concentrated in vacuo giving 1.05 g. of oily product. This material was chromatographed on 50 g. of silica gel. Elution with 2:1 parts by volume and 1:1 parts by volume hexane-ether afforded 0.844 g. of a pale yellow oil. Evaporative distillation gave rac. Z-1-benzyloxy-2-methyl-5-hepten-4-ol as a colorless oil, b.p. 113°-123° C. (bath temperature) (0.25 mm Hg.).

Workup

  1. additionA mixture of 1 g
  2. filtrationThe catalyst was filtered
  3. washwashed with hexane
  4. concentrationthe combined filtrate and washes were concentrated in vacuo
  5. customgiving 1.05 g
  6. customThis material was chromatographed on 50 g
  7. washElution with 2:1 parts by volume and 1:1 parts by volume hexane-ether
  8. customafforded 0.844 g
  9. distillationEvaporative distillation

Sources & evidence

ORD record
ord-72721e8235b6484c88b8f20c9918f3e3
Source dataset
uspto-grants-1979_10
Patent number
US04172958

Reaction notes

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