Borane;tetrahydrofuran → 2-(4-Hydroxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester

HRID 1628169

Reaktionsgleichung

Reaktionsgleichung von HRID 1628169
[Cl:1][C:2]([Cl:25])([Cl:24])[CH2:3][O:4][C:5](=[O:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.B.C1COCC1>C1COCC1>[Cl:25][C:2]([Cl:1])([Cl:24])[CH2:3][O:4][C:5](=[O:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 668652432-(4-Carboxy-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester

Produkt 1

HCID 668652542-(4-Hydroxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl esterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(4-Carboxy-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester (80 mg, 0.191 mmol) in THF (1 mL) at 0° C. was added dropwise BH3-THF (0.4 mL, 1.0M solution in THF). The reaction was stirred at 0° C. for 0.5 h after the addition was complete, thereafter the cooling bath was removed and the reaction was stirred for 2 h at rt. The reaction was quenched at 0° C. by careful addition of THF/H2O, 80/20 followed by dropwise addition of 2M HCl. The mixture was stirred for an additional 10 minutes and thereafter diluted with water. THF was removed and the water phase was extracted with DCM and the combined organic phase was dried through a phase separator and concentrated to give the titled compound (70 mg, 91%) as an oil; 1H NMR (400 MHz, CDCl3): δ 4.53 (s, 2H), 4.64 (s, 2H), 4.94 (s, 2H), 7.19-7.30 (m, 5H), 7.30-7.36 (m, 1H), 7.37-7.44 (m, 1H), 8.06 (d, 1H).

Aufarbeitung

  1. additionafter the addition
  2. customthe cooling bath was removed
  3. stirringthe reaction was stirred for 2 h at rt
  4. customThe reaction was quenched at 0° C. by careful addition of THF/H2O, 80/20
  5. additionfollowed by dropwise addition of 2M HCl
  6. stirringThe mixture was stirred for an additional 10 minutes
  7. additiondiluted with water
  8. customTHF was removed
  9. extractionthe water phase was extracted with DCM
  10. customthe combined organic phase was dried through a phase separator
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-79912b9f8e914994ae18e2e79eadbdd6
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785681B2

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