Tetrahydrofuran → HCID 86751987, compound

HRID 727553Notes

Reaction equation

HRID 727553 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][C:4]1([C:12]([CH3:14])=[CH2:13])[CH2:9][CH:8](CO)[O:7][C:5]1=[O:6].[OH-].[Na+].C1C[O:21]CC1.I([O-])(=O)(=O)=O.[Na+]>O>[CH3:1][CH:2]([CH3:15])[CH2:3][C@:4]1([C:12]([CH3:14])=[CH2:13])[CH2:9][C@H:8]([OH:21])[O:7][C:5]1=[O:6]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 23667635Sodium periodateHCID 86751988HCID 86751988, compound

Product 1

HCID 86751987HCID 86751987, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of [S-(R*,R*)]-α-(2-methylpropyl)-α-(propen-2-yl)-γ-hydroxymethyl-γ-butyrolactone (682 mg, 3.21 mmol), NaOH (350 mg, 8.75 mmol), THF (40 mL), and H2O (10 mL) is stirred for 19 hours at room temperature. Additional NaOH (114 mg, 2.85 mmol) is added after 16 hours. The mixture is concentrated and the residue taken up into MeOH (43 mL). A solution of sodium periodate (862 mg, 4.03 mmol) and H2O (4.3 mL) is added and the mixture stirred at room temperature for 3 hours. After concentration, the aqueous residue is acidified (HCl) and extracted with CH2Cl2 (3×40 mL). The organic layers are dried (MgSO4), filtered, and concentrated to provide 625 mg (98%) of the title compound as a semi-solid.

Workup

  1. concentrationThe mixture is concentrated
  2. stirringthe mixture stirred at room temperature for 3 hours
  3. concentrationAfter concentration
  4. extractionextracted with CH2Cl2 (3×40 mL)
  5. dry with materialThe organic layers are dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bc34b2e269114276a2521f3cb7a72b03
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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