Water → HCID 59178220, compound

HRID 1643414Notes

Reaction equation

HRID 1643414 reaction equation
[C@@H:1]12[O:6][C@@H:5]1[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]2.[OH2:11].[Na+].[Cl-]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[OH:6][C@H:1]1[C@H:5]([OH:11])[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 10374550(1R,3s,5S)-methyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate

Product 1

HCID 59178220HCID 59178220, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl (1S,5R)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (8 g, 56.3 mmol) and tetrabutylammonium bisulfate (1.911 g, 5.63 mmol) were suspended in THF (5 ml) and water (75 ml) and allowed to stir for 48 hrs. Added solid NaCl and extracted with three 250 ml portions of EtOAc. Added 100 ml Hexane washed with brine and dryed over sodium sulfate. Silca gel chromatography on a 50 g Biotage SNAP cartridge with 40-60% acetone-hexane to give title product as a clear oil. 1H NMR (500 MHz, CDCl3) δ 1.89-2.03 (m, 3H), δ 2.26-2.42 (m, 3H), δ 3.08-3.15 (m, 1H), δ 3.74 (s, 3H), δ 4.06 (m, 1H), δ 4.23 (m, 1H)

Workup

  1. extractionextracted with three 250 ml portions of EtOAc
  2. additionAdded 100 ml Hexane
  3. washwashed with brine

Sources & evidence

ORD record
ord-46027e02f8f8415b87de3bd3c77d294a
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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