Aluminium lithium hydride → HCID 58557598, compound

HRID 1969541Notes

Reaction equation

HRID 1969541 reaction equation
[CH2:1]([CH:3]1[CH2:7][CH:6]([C:8](OC)=[O:9])[CH2:5][CH:4]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:1]([CH:3]1[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5][CH:4]1[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58557941HCID 58557941, compound

Product 1

HCID 58557598HCID 58557598, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 3-tert-butyl 1-methyl 4-ethylcyclopentane-1,3-dicarboxylate (3.88 g, 15.1 mmol, Preparation #11, Step B) in Et2O (150 mL) was cooled to about −40° C. LAH (2 N in THF, 8.32 mL, 16.6 mmol) was added dropwise. The reaction mixture was stirred at about −40° C. for about 1 hour. The reaction mixture was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (3×50 mL). The combined organic extracts were concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc/heptane to give tert-butyl 2-ethyl-4-(hydroxymethyl)cyclopentanecarboxylate (1.00 g, 29%) as a brown oil: LC/MS (Table 1, Method a) Rt=2.37 min; MS m/z: 229 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (3×50 mL)
  2. customThe crude material was purified by silica gel chromatography
  3. washeluting with a gradient of 0-100% EtOAc/heptane

Sources & evidence

ORD record
ord-d6ee8ff708d14f6d99e31032ef559380
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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