6-Benzyloxy-1-hexanol → 6-Benzyloxyhexanal

HRID 1875290Notes

Reaction equation

HRID 1875290 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH2:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[O:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 27847636-Benzyloxy-1-hexanolHCID 178418287HCID 178418287, compound

Product 1

HCID 3898776-Benzyloxyhexanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesis of [18F]-FCPHA was performed using the following method. PCC (pyridinium chlorochromate; 24.8 g, 115.2 mmol) was slowly added in portions to a solution of 6-benzyloxy-1-hexanol (20 g, 96 mmol) in 200 ml of methylene chloride at room temperature (25° C., RT). The black mixture was stirred for 2 hours, and filtered through 50 g of silica gel. The solvent was removed and the crude oil was separated chromatographically on silica gel using a mixture of hexane:ethyl acetate at a ratio of 90:10. This yielded the aldehyde equivalent, 6-benzyloxy-1-hexanal, at a scale of 14 g (70%).

Workup

  1. filtrationfiltered through 50 g of silica gel
  2. customThe solvent was removed
  3. customthe crude oil was separated chromatographically on silica gel using
  4. additiona mixture of hexane

Sources & evidence

ORD record
ord-d9a435f588fd42cf8ed00c7806de8c2d
Source dataset
uspto-grants-2012_11
Patent number
US08309053B2

Reaction notes

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