Ethanol → Ethyl 7-(3-hydroxypropoxy)-2-ethylchromane-2-carboxylate

HRID 479636Notes

Reaction equation

HRID 479636 reaction equation
C(O)C.C([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][C:22]([CH2:31][CH3:32])([C:26]([O:28][CH2:29][CH3:30])=[O:27])[O:23]2)=[CH:18][CH:17]=1)C1C=CC=CC=1>[Pd].O>[OH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][C:22]([CH2:31][CH3:32])([C:26]([O:28][CH2:29][CH3:30])=[O:27])[O:23]2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 22737356Ethyl 7-(3-benzyloxypropoxy)-2-ethylchromane-2-carboxylate

Product 1

HCID 22737369Ethyl 7-(3-hydroxypropoxy)-2-ethylchromane-2-carboxylateYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To an 80 ml ethanol solution of ethyl 7-(3-benzyloxypropoxy)-2-ethylchromane-2-carboxylate (3.76 g, 9.5 mmol) was added water 4 ml and 10% Pd/C 300 mg. This solution was placed in a Parr shaker and was shaken under hydrogen atmosphere (50 psi) overnight. The catalyst was removed by filtration through a pad of celite. The filtrate was concentrated and chromatographed on silica gel. Elution with 30% AcOEt/hexanes gave the title compound 2.88 g as colorless syrup (quant.).

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. customchromatographed on silica gel
  4. washElution with 30% AcOEt/hexanes

Sources & evidence

ORD record
ord-531d8e49132d48a7b2fb86a614eb711a
Source dataset
uspto-grants-2003_11
Patent number
US06645997B2

Reaction notes

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