Lithium hydroxide, monohydrate → HCID 53700552, compound

HRID 1169187Notes

Reaction equation

HRID 1169187 reaction equation
C[O:2][C:3](=[O:18])[CH:4]([CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C1(C2COC(=O)C2)CCCC1.O[Li].O>C(O)(C)C.O>[C:9]([O:8][C:6](=[O:7])[CH2:5][CH:4]([CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1)[C:3]([OH:18])=[O:2])([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86759176HCID 86759176, compound

Product 1

HCID 53700552HCID 53700552, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

Preparation of 4-Cyclopentyl-dihydro-furan-2-one 2-Cyclopentyl-succinic acid 4-tert-butyl ester 1-methyl ester (13.4 g, 52.3 mmol) and LiOH.H2O (2.8 g, 66.7 mmol) are stirred in 200 mL of 3:1 isopropanol/H2O at room temperature overnight. The isopropanol is evaporated, and the aqueous solution is extracted with Et2O (3×100 mL). The aqueous phase is acidified to pH=4 with saturated KH2PO4 and extracted with Et2O (3×100 mL). The Et2O is dried over MgSO4 and evaporated to give 8.6 g (68% yield) of 2-cyclopentyl-succinic acid 4-tert-butyl ester. NMR (1H, 400 MHz, CDCl3) δ1.1-1.3 (2H, m); 1.4 (9H, s); 1.5 (4H, m); 1.7 (2H, m); 1.9 (1H, m); 2.4 (1H, dt); 2.6 (2H, m). The product is carried on.

Workup

  1. customThe isopropanol is evaporated
  2. extractionthe aqueous solution is extracted with Et2O (3×100 mL)
  3. extractionextracted with Et2O (3×100 mL)
  4. dry with materialThe Et2O is dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-3555a25a0ec6422c956a3c162d821cd7
Source dataset
uspto-grants-2003_09
Patent number
US06627771B1

Reaction notes

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