4-(Hydroxymethyl)benzeneboronic acid → 1-[2-(4-Hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene

HRID 1376532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376532
Br[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>>[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH2:6][CH2:5][CH2:4][C:3]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)=[CH:19][CH:18]=1

Komponenten

3

Edukt 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 102650591-(2-Bromocyclopenten-1-yl)-4-(methylthio)benzene

Produkt 1

HCID 229172821-[2-(4-Hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzeneAusbeute 92,5 %

Versuchsvorschrift

Following the synthetic procedure outlined in Step 3 of Example 1, 250 mg (0.93 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylthio) benzene (Example 1, Step 2) was reacted with 290 mg (1.9 mmol) of 4-hydroxymethylphenylboronic acid (Step 1). Purification by silica gel chromatography (MPLC) with ethyl acetate/hexane (1:4) gave 255 mg (92%) of 1-[2-(4-hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylthio)benzene as a solid: mp 82°-85° C.; NMR (CDCl3) δ2.04 (m, J=7 Hz, 2H), 2.45 (s, 3H), 2.88 (t, J=7 Hz, 4H), 4.64 (s, 2H), 7.08 (s, 4H), (m, 2H), 7.15-7.25 (m, 4H).

Aufarbeitung

  1. customPurification by silica gel chromatography (MPLC) with ethyl acetate/hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-cd4c8323a72e49a7beacc66ddc535365
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663180

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