Sodium Hydroxide → HCID 58557273, compound

HRID 1969562Notes

Reaction equation

HRID 1969562 reaction equation
[CH2:1]([C@@H:3]1[CH2:7][C:6](=[O:8])[CH2:5][C@@H:4]1[C:9](OCC)=[O:10])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH2:1]([C@H:3]1[C@@H:4]([CH2:9][OH:10])[CH2:5][CH:6]([OH:8])[CH2:7]1)[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 58557854HCID 58557854, compound

Product 1

HCID 58557273HCID 58557273, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,2R)-ethyl 2-ethyl-4-oxocyclopentanecarboxylate (5 g, 27.1 mmol, Example #22 step B) in THF (100 mL) at about −78° C. was added LAH (2 M in THF, 54.3 mL, 109 mmol). After about 1 h, the reaction mixture was allowed to warm to rt slowly. After about 4 h, water (4.8 mL) followed by aqueous NaOH (15% w/v, 4.8 mL) followed by water (9.6 mL) was added to the reaction mixture. After about 15 h, anhydrous Na2SO4 was added and the slurry was filtered and concd in vacuo to provide crude (3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentanol (3.9 g, 100%) as an oil which was used without further purification. LC/MS (Table 1, Method a) Rt=2.40 min; MS m/z: 145 (M+H)+.

Workup

  1. waitAfter about 4 h
  2. additionwas added to the reaction mixture
  3. waitAfter about 15 h
  4. filtrationthe slurry was filtered

Sources & evidence

ORD record
ord-9f4eea00ada34cefaeb07bbfb443fb83
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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