Acetic Acid → HCID 69629020, compound

HRID 987299Notes

Reaction equation

HRID 987299 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].CC(C)([O-])C.[K+].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.C1(C)C=CC=CC=1>[CH2:26]([O:25][C:23](=[O:24])/[C:22](/[O:21][CH2:20][CH2:19][O:18][CH3:17])=[CH:13]/[C:12]1[CH:15]=[CH:16][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 22988705Benzyl (2-methoxyethoxy)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 69629020HCID 69629020, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

4-(Benzyloxy)benzaldehyde (3.00 g; 14.0 mmole) and benzyl 2-(2-methoxyethoxy)acetate (4.23 g; 17.0 mmole) were dissolved in dry tetrahydrofuran (100 ml) and cooled to −20° C. Potassium tert-butoxide (1.91 g; 17.0 mmole) dissolved in dry tetrahydrofuran (10 ml) was slowly added and the reaction was stirred over night at −20° C. The reaction was quenched with acetic acid (0.85 g; 14.0 mmole). The crued product was isolated, redissolved in toluene and refluxed over night with p-toluenesulfonic acid (0.24 g; 1.4 mmole) in a Dean-Stark apparatus to separate the water. The solution was cooled, washed with sodium hydrogene carbonate, dried with magnesium sulfate and evaporated. Purification of the crude product with preparativ HPLC (Kromasil C8, 10 μm, 50×500 mm) using acetronitrile (50-70%) in ammonium acetate buffer (pH 7) as mobil phase gave 1.83 g (29% yield) of (Z)-3-[4-(benzyloxy)phenyl]-2-(2-methoxyethoxy)-2-propenoic acid benzyl ester.

Workup

  1. additionwas slowly added
  2. customThe crued product was isolated
  3. customto separate the water
  4. temperatureThe solution was cooled
  5. washwashed with sodium hydrogene carbonate
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customPurification of the crude product with preparativ HPLC (Kromasil C8, 10 μm, 50×500 mm)

Sources & evidence

ORD record
ord-4dc2d32b5ce640448b64574906ca2b5a
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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