Diethyl Ether → HCID 57111947, compound

HRID 1492680Notes

Reaction equation

HRID 1492680 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C@H:11]1[C@@H:16]2[C@H:17]([CH3:20])[CH2:18][CH2:19][C@@H:15]2[C:14]([C:21](OC)=O)=[CH:13][O:12]1)(=O)C.CCOCC.[OH-].[Na+]>O1CCCC1>[OH:10][CH2:11][C@@H:16]1[C@H:17]([CH3:20])[CH2:18][CH2:19][C@@H:15]1[C:14](=[CH2:21])[CH2:13][OH:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131718288HCID 131718288, compound

Product 1

HCID 57111947HCID 57111947, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.0 g (0.21 mol) of lithium aluminum hydride was suspended in 100 ml of anhydrous tetrahydrofuran, and 150 ml of an anhydrous tetrahydrofuran solution of methyl (1S, 4aS, 7R, 7aR)-1-acetoxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate obtained in Definite Example 52 (14.5 g, 0.057 mol) was added dropwise while being cooled by ice and stirred. The temperature was returned to room temperature and the reaction mixture was stirred for 3 hours. After 300 ml of ether was added, 1N sodium hydroxide solution was further added dropwise. After insoluble matters were filtered by celite, concentration was carried out and the residual substance was purified by chromatography using silica gel. When the solvent of the fraction obtained from ether:ethyl acetate=9:1 eluent was distilled off, and a colorless oily substance was obtained, i.e., 2-[(1S, 2R, 3R)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]-2-propen-1-ol (5.55 g, yield=57.2%). This 2-[(1S, 2R, 3R)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]-2-propen-1-ol had the following physicochemical properties.

Workup

  1. additionwas added dropwise
  2. temperaturewhile being cooled by ice
  3. customwas returned to room temperature
  4. stirringthe reaction mixture was stirred for 3 hours
  5. filtrationAfter insoluble matters were filtered by celite, concentration
  6. customthe residual substance was purified by chromatography
  7. customWhen the solvent of the fraction obtained from ether
  8. distillationethyl acetate=9:1 eluent was distilled off
  9. customa colorless oily substance was obtained

Sources & evidence

ORD record
ord-ed9bee3eead24ec69f1db7c36ebff2ae
Source dataset
uspto-grants-1994_12
Patent number
US05374653

Reaction notes

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