Lithium hydroxide, monohydrate → 11-(1-Carboxycyclobutyl)-2,2-dimethyl-7-oxoundecanoic acid

HRID 969004Notes

Reaction equation

HRID 969004 reaction equation
C([O:3][C:4]([C:6]1([CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:27])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22]CC)=[O:21])[CH2:9][CH2:8][CH2:7]1)=[O:5])C.O[Li].O>>[C:4]([C:6]1([CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:27])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:25])([CH3:26])[C:20]([OH:22])=[O:21])[CH2:7][CH2:8][CH2:9]1)([OH:5])=[O:3]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68579358Ethyl 11-[1-(ethoxycarbonyl)cyclobutyl]-2,2-dimethyl-7-oxoundecanoate

Product 1

HCID 1164555911-(1-Carboxycyclobutyl)-2,2-dimethyl-7-oxoundecanoic acid

Procedure

Compound 107e was prepared likewise Method D starting from 106e (8.83 g, >90% pure by 1H NMR, 20.8 mmol) and LiOH.H2O (2.91 and 1.94 g after 18 h, 69.4 and 46.2 mmol) to give, after recrystallized from iPr2O/heptane, 7e (5.19 g, 76%) as a white solid. mp=53-55° C. 1H NMR: δ 10.80 (br s, 2H), 2.50-2.35 (m, 2H), 2.39 (t, J=7.2 Hz, 4H), 1.98-1.74 (m, 6H), 1.65-1.49 (m, 6H), 1.31-1.11 (m, 4H), 1.18 (s, 6H). 13C NMR: δ 210.6, 184.3, 183.4, 47.6, 42.7, 42.6, 42.2, 40.5, 37.8, 30.1 (2×), 25.1 (2×), 24.8, 24.7, 24.2, 24.1, 15.7.

Workup

  1. customto give
  2. customafter recrystallized from iPr2O/heptane, 7e (5.19 g, 76%) as a white solid

Sources & evidence

ORD record
ord-bec9fa2abdef4b5fbe514aaae9b9eedd
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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