Ethanol → HCID 66579331, compound

HRID 73635Notes

Reaction equation

HRID 73635 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH:6]2[CH2:11]/[CH:12]=[CH:13]/[C:14](OC)=[O:15])[O:4][CH2:3][CH2:2]1.[Li+].[Cl-].[BH4-].[Na+].CCO>C1COCC1>[O:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH:6]2[CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 86668659HCID 86668659, compound

Product 1

HCID 66579331HCID 66579331, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl (2E)-4-(1,4,8-trioxaspiro[4.5]dec-6-yl)but-2-enoate (0.747 g, 3.08 mmol) in THF (9 mL) was added anhydrous LiCl (0.261 g, 6.71 mmol) and Sodium borohydride (0.233 g, 6.17 mmol). EtOH (12 mL) was then added slowly and the mixture was stirred at rt overnight. It was cooled to 0° C. and quenched with 10% aqueous citric acid. The organic layer was then concentrated and the mixture was diluted with water and CH2Cl2. Extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.91-4.05 (m, 4H), 3.77-3.90 (m, 2H), 3.60-3.70 (m, 3H), 3.44 (dd, 1H, J=8.8 Hz, 11.0 Hz), 1.14-1.82 (m, 9H).

Workup

  1. temperatureIt was cooled to 0° C.
  2. customquenched with 10% aqueous citric acid
  3. concentrationThe organic layer was then concentrated
  4. additionthe mixture was diluted with water and CH2Cl2
  5. extractionExtracted 3× with CH2Cl2
  6. dry with materialThe combined organics were dried (anhd. Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1b7c99f029eb4085b54316bc544dd6a9
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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