Lithium hydroxide, monohydrate → HCID 11545669, compound

HRID 873264Notes

Reaction equation

HRID 873264 reaction equation
C([O:5][C:6]([C:8]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2([C:29]([O:31]CCCC)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])CCC.O[Li].O>>[C:29]([C:24]1([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18](=[O:36])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:8]2([C:6]([OH:7])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:25][CH2:26][CH2:27][CH2:28]1)([OH:31])=[O:30]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21932042HCID 21932042, compound

Product 1

HCID 11545669HCID 11545669, compound

Procedure

Compound 107m was prepared likewise Method D starting from 106m (21.03 g, 90% pure by 1H NMR, 37.3 mmol) and LiOH.H2O (7.83 g, 187 mmol) to give, after recrystallization from iPr2O/heptane, 107m (12.15 g, 83%) as white granules. mp=78-85° C. 1H NMR: δ 2.37 (t, J=7.4 Hz, 4H), 2.18-2.10 (m, 4H), 1.65-1.45 (m, 20H), 1.29-1.25 (m, 8H). 13C NMR: δ 211.5, 184.8 (2×), 54.0 (2×), 42.4 (2×), 38.9 (2×), 35.9 (4×), 29.2 (2×), 25.5 (2×), 24.9 (4×), 23.5 (2×). Anal. calcd for C23H38O5: C, 70.02; H, 9.71. found: C, 70.37; H, 9.72.

Workup

  1. customto give
  2. customafter recrystallization from iPr2O/heptane, 107m (12.15 g, 83%) as white granules

Sources & evidence

ORD record
ord-6363b7f690ab4ceb8a6f18914729bf02
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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