Lithium Hydroxide → HCID 178424241, compound

HRID 59772Notes

Reaction equation

HRID 59772 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][C@H:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:17][CH2:16]3)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Li+]>O1CCCC1.C(OC)(C)(C)C.Cl>[C:24]1([CH3:29])[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C@@H:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([O:12][C@H:9]3[CH2:8][CH2:7][C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)[CH:14]=2)[O:19]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 178472461HCID 178472461, compound

Product 1

HCID 178424241HCID 178424241, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

0.75 g (1.9 mmol) of trans-4-((S)-2-o-tolyl-chroman-6-yloxy)-cyclohexanecarboxylic acid ethyl ester was dissolved in 10 ml of tetrahydrofuran. 94 mg (3.9 mmol) lithium hydroxide (dissolved in 2 ml of water) were added. The solution was stirred at room temperature overnight until no starting material could be detected by RP-HPLC. The solution was diluted with methyl tert-butyl ether, and 2N hydrochloric acid was added until a pH of 2. After phase separation, the organic layer was dried over magnesium sulfate and the solvent was evaporated. The resulting product crystallized on standing to yield 0.65 g of the title compound.

Workup

  1. additionwas added until a pH of 2
  2. customAfter phase separation
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe resulting product crystallized

Sources & evidence

ORD record
ord-1eb2ed061c3f4d97b82abd532d27c5e6
Source dataset
uspto-grants-2016_09
Patent number
US09440941B2

Reaction notes

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