Acetic Acid → HCID 58560719, compound

HRID 536775Notes

Reaction equation

HRID 536775 reaction equation
CO[CH:3]([O:22]C)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C@@H:11]([OH:21])[C@H:12]([OH:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:6][CH:5]=1.[C:24](O)(=O)[CH3:25].[C:28]([O-])(O)=O.[Na+]>C1COCC1>[CH2:13]([C@H:12]1[O:20][C:24]([CH3:25])([CH3:28])[O:21][C@@H:11]1[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH:3]=[O:22])=[CH:9][CH:8]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 46184655HCID 46184655, compound

Product 1

HCID 58560719HCID 58560719, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,3R)-1-(4-(dimethoxymethyl)phenyl)decane-2,3-diol (M) (0.38 g, 1.17 mmol) in THF (12 mL) at room temperature was added aqueous acetic acid (6.2 mL, 2.5 M). The reaction mixture was stirred for two hours until TLC indicated completion of the reaction at which time saturated aqueous NaHCO3 was added, and the mixture extracted with ether. The collected organic layers were washed with brine, dried with MgSO4, filtered, and concentrated to yield the free aldehyde (0.309 g, 1.11 mmol, 95%). The crude free aldehyde was dissolved in acetone (5 mL) and to this mixture was added p-toluenesulfonic acid (33 mg, 0.17 mmol). The reaction mixture was stirred overnight, at which time TLC indicated completion of the reaction. Upon completion, triethylamine (24 μL, 0.17 mmol) was added and solvent was evaporated. Flash chromatography of the residue gave the title compound (0.26 g, 0.82 mmol, 74%). 1H NMR (CDCl3, 300 MHz) δ 9.90 (1H, s), 7.82 (2H, d, J=8.1 Hz), 7.42 (2H, d, J=7.8 Hz), 3.88-3.83 (1H, m), 3.70-3.65 (1H, m), 2.94 (2H, d, J=5.7 Hz), 1.51-1.29 (12H, m), 1.37 (3H, s), 1.35 (3H, s), 0.88 (3H, t, J=4.8 Hz); LRMS (APCI+) calcd for C20H30O3 [M+H]: 319.2; found 319.5

Workup

  1. additionwas added
  2. extractionthe mixture extracted with ether
  3. washThe collected organic layers were washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-644e52b908fe43d1b9aaa485a393092d
Source dataset
uspto-grants-2014_10
Patent number
US08859615B2

Reaction notes

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