Reaction #75248

Reaction equation

1,1,1-trifluoro-5-bromopentane

1-chloro-9,9,9-trifluoro-4-nonanol

1-chloro-9,9,9-trifluoro-4-nonanone

1-chloro-4-acetoxy-9,9,9-trifluorononane

ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoate

ethyl 4-(4-acetyl-8-acetoxy-13,13,13-trifluorotridecyl)benzoate

amyl bromide

ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxy-13,13,13-trifluorotridecyl)benzoate

→

4-(4-acetyl-8-hydroxy-13,13,13-trifluorotridecyl)benzoic acid

Conditions

Workup

1. 1
   OtherThe synthesis of this compound
2. 2
   OtherSubsequent steps afford in order

Procedure

The synthesis of this compound is carried out as described in Example 1, except that in Step B(1) an equivalent amount of 1,1,1-trifluoro-5-bromopentane is substituted for amyl bromide. The product of Step B(1) thus becomes 1-chloro-9,9,9-trifluoro-4-nonanone. Subsequent steps afford in order: Step B(2), 1-chloro-9,9,9-trifluoro-4-nonanol; Step B(3), 1-chloro-4-acetoxy-9,9,9-trifluorononane; Step C, ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoate; Step D, ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxy-13,13,13-trifluorotridecyl)benzoate (by substituting 1-chloro-4-acetoxy-9,9,9-trifluorononane for 1-chloro-4-acetoxynonane); Step E, ethyl 4-(4-acetyl-8-acetoxy-13,13,13-trifluorotridecyl)benzoate; and Step F, 4-(4-acetyl-8-hydroxy-13,13,13-trifluorotridecyl)benzoic acid, obtained as a viscous yellow oil.

Source