1,1-Diethyl cyclopent-3-ene-1,1-dicarboxylate → [1-(Hydroxymethyl)cyclopent-3-en-1-yl]methanol

HRID 2203676Notes

Reaction equation

HRID 2203676 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:17](OCC)=[O:18])([C:12](OCC)=[O:13])[CH2:11][CH:10]=[CH:9][CH2:8]1>O1CCCC1.O.[OH-].[Na+]>[C:7]1([CH2:17][OH:18])([CH2:12][OH:13])[CH2:11][CH:10]=[CH:9][CH2:8]1

Participants

6

Reactant 2

HCID 109875691,1-Diethyl cyclopent-3-ene-1,1-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 14656537[1-(Hydroxymethyl)cyclopent-3-en-1-yl]methanolYield 177.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
26 °C

Procedure

To an ice-cooled suspension of lithium aluminum hydride (25.54 g, 672.8 mmol) in tetrahydrofuran (2 L) was added a solution of diethyl cyclopent-3-ene-1,1-dicarboxylate (42.0 g, 198 mmol) in tetrahydrofuran (100 mL) over 30 min. The reaction mixture was warmed to 26° C. After 2 h, the reaction was diluted sequentially with water (26 mL), 3M aqueous sodium hydroxide solution (26 mL), and water (78 mL). The mixture was stirred at 0° C. for 15 min and filtered. The filtrate was concentrated to afford product as a colorless oil (45 g, 89% yield).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e67ff5d976444744a17c3ee92f3e7b98
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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