Hydrochloric Acid → HCID 53710425, compound

HRID 1086717Notes

Reaction equation

HRID 1086717 reaction equation
[C:1]([C:4]1([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:7][CH2:6][CH2:5]1)([OH:3])=[O:2].C([N-]C(C)C)(C)C.[Li+].[CH3:26][O:27][CH2:28]Cl.Cl>O1CCCC1.O>[C:14]([O:13][C:11](=[O:12])[CH:10]([CH2:26][O:27][CH3:28])[CH2:9][C:4]1([C:1]([OH:3])=[O:2])[CH2:8][CH2:7][CH2:6][CH2:5]1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 2724682Lithium diisopropylamideHCID 11010130t-Butyl 3-(1-carboxycyclopentyl)propanoate

Product 1

HCID 53710425HCID 53710425, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of t-butyl 3-(1-carboxycyclopentyl)propanoate (1.0 g, 4.13 mmole) in dry tetrahydrofuran was added to a stirred solution of lithium diisopropylamide (9.29 mmole) in dry tetrahydrofuran (50 ml) at -78° C. under nitrogen. After 0.5 hours, chloromethyl methyl ether (0.53 g, 6.58 mmole) was added and the mixture was allowed to warm to room temperature over 16 hours. The solution was poured into water, acidified to pH 3 with 2N hydrochloric acid and extracted with ethyl acetate (3×50 ml). The organic layer was separated, dried over magnesium sulphate and evaporated to give a colourless oil that was chromatographed on silica gel eluting with a mixture of diethyl ether and dichloromethane (1:9-1:4 by volume). Evaporation of the appropriate fractions gave the title compound as a colourless oil (0.78 g, 66%). Found: C,62.75; H,8.94. C15H26O5 requires: C,62.91; H,9.15%.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customto give a colourless oil that
  6. customwas chromatographed on silica gel eluting with a mixture of diethyl ether and dichloromethane (1:9-1:4 by volume)
  7. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-0d19eca6184a458c8b6eefc633af3cab
Source dataset
uspto-grants-1991_07
Patent number
US05030654

Reaction notes

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