Toluene → HCID 86758725, compound

HRID 2300411Notes

Reaction equation

HRID 2300411 reaction equation
[O:1]=[C:2]1[O:8][CH2:7][CH2:6][CH:5]2[CH:3]1[CH:4]2[C:9]([O:11][CH2:12][CH3:13])=[O:10].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[OH:1][CH:2]1[O:8][CH2:7][CH2:6][CH:5]2[CH:3]1[CH:4]2[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 86758724HCID 86758724, compound

Product 1

HCID 86758725HCID 86758725, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl (1SR,6SR,7SR)-2-oxo-3-oxa-bicyclo[4.1.0]heptane-7-carboxylate (15.2 g, 82.8 mmol) in anhydrous tetrahydrofuran (300 mL) at −78° C. and under argon, a 1.5 M solution of diisobutylaluminium hydride in toluene (82.8 mL, 124.2 mmol) in anhydrous tetrahydrofuran (150 mL) at −78° C. under an argon atmosphere was added dropwise via cannula. The solution was stirred for six hours at this temperature and then diluted with ethyl acetate (200 mL) and quenched with a saturated aqueous solution of sodium tartrate (200 mL). The resulting mixture was stirred at room temperature overnight. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated in vacuo. The residue was purified by column chromatography using ethyl acetate and hexane 1:2 as eluent to afford 12.3 g (85% yield) of (2RS) and (2SR) ethyl (1SR,6RS,7SR)-2-hydroxy-3-oxa-bicyclo[4.1.0]heptane-7-carboxylate as a colorless oil, which exist with their corresponding open hydroxyaldehyde forms.

Workup

  1. customquenched with a saturated aqueous solution of sodium tartrate (200 mL)
  2. stirringThe resulting mixture was stirred at room temperature overnight
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-623376886c3f4770a5bab8b5fdf0fb53
Source dataset
uspto-grants-2002_12
Patent number
US06498180B1

Reaction notes

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