Tetrahydrofuran → 6-Chloro-2-(4-ethoxyphenyl)hexanoic acid

HRID 1803229Notes

Reaction equation

HRID 1803229 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.[Cl:29][CH2:30][CH2:31][CH2:32][CH2:33]I>>[Cl:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 78631Benzeneacetic acid, 4-ethoxy-HCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 581101156-Chloro-2-(4-ethoxyphenyl)hexanoic acidYield 37%

Procedure

Step AAN (1): 2-(4-Ethoxyphenyl)acetic acid (2.00 g, 11.1 mmol) was deprotonated with NaHMDS 2.0 M in THF (12.5 mL, 25.0 mmol) and reacted with 1-chloro-4-iodobutane (1.49 mL, 12.2 mmol) using a procedure analogous to Step AC (1) and after silica gel column chromatography (30-80% EtOAc/hexanes) afforded 6-chloro-2-(4-ethoxyphenyl)hexanoic acid (1.10 g, 4.06 mmol, 37% yield) as a pale-yellow oil. LC-MS (M+Na)+ 293.1.

Sources & evidence

ORD record
ord-b709ff0979e74d91833c4d17048643cc
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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