Water → 3,4-Dihydro-1H-2-benzopyran-1-ol

HRID 233626

Reaktionsgleichung

Reaktionsgleichung von HRID 233626
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S([O-])(=O)=O)=[CH:4][CH:3]=1.[NH+]1C=CC=CC=1.C(N(CC)CC)C.[NH4+].[Cl-].C1[CH2:32][O:31][CH2:30]C1>>[OH:1][CH:30]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:32][O:31]1

Komponenten

6

Edukt 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 136137083,4-Dihydro-1H-2-benzopyran-1-olAusbeute 95 %

Versuchsvorschrift

To a solution of methyl-3-(2'-formyl-3'-6'-dimethoxy)phenyl-2-methoxyisopropyloxy-propionate (4.2 g, 12.4 mmol) in THF (75 ml) containing water (4 ml) was added pyridinium p-toluenesulfonate (230 mg). After stirring at room temperature for 1.75 hours, triethylamine (3 ml) and saturated NH4Cl solution (60 ml) were added. THF was removed at 25° C. and the mixture was extracted with ether (3×150 ml). Ether extract was washed with brine, dried and evaporated yielding 3.9 g of 1-hydroxyisochroman (95%) (quite pure from NMR spectrum). (MP. 127°-129° C.)

Aufarbeitung

  1. customTHF was removed at 25° C.
  2. extractionthe mixture was extracted with ether (3×150 ml)
  3. extractionEther extract
  4. washwas washed with brine
  5. customdried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1a91f95f18444534942176066df07556
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05593970

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