2-Methyl-1-benzothiophene-7-carboxylic acid → HCID 58566649, Verbindung

HRID 1876363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876363
[CH3:1][C:2]1[S:6][C:5]2[C:7]([C:11](O)=[O:12])=[CH:8][CH:9]=[CH:10][C:4]=2[CH:3]=1>O1CCCC1>[CH3:1][C:2]1[S:6][C:5]2[C:7]([CH2:11][OH:12])=[CH:8][CH:9]=[CH:10][C:4]=2[CH:3]=1

Komponenten

3

Edukt 1

HCID 126239032-Methyl-1-benzothiophene-7-carboxylic acid

Produkt 1

HCID 58566649HCID 58566649, VerbindungAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The carboxylic acid (509) (0.240 g, 1.25 mmol) was dissolved in anhydrous tetrahydrofuran (12 mL) and cooled to 0° C. under nitrogen. BH3-tetrahydrofuran complex (3.12 mL, 3.12 mmol, 1.0 M in tetrahydrofuran) was added slowly. After the addition was complete, the solution was allowed to warm to room temperature and stirred for an additional 1 hour. The solution was cooled to 0° C. and quenched by the addition of methanol (5 mL) followed by a saturated sodium sulfate aqueous solution (5 mL). The mixture was diluted with ethyl acetate and washed with brine and dried over sodium sulfate, filtered, and concentrated in vacuo to provide (2-methylbenzo[b]thiophen-7-yl)methanol (510) (0.203 g, 91.2%) as a colorless oil.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. temperatureThe solution was cooled to 0° C.
  4. customquenched by the addition of methanol (5 mL)
  5. additionThe mixture was diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e19d6285a0a54850b865c426b87ce4c1
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309600B2

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