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Hydrochloric Acid → HCID 58593383, Verbindung

HRID 916994
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 916994
[C:1]([C:5]1[CH:10]=[C:9]([S:11][C:12]([S:15][C:16]2[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([O:26][CH2:27][CH2:28][CH2:29][C@@H:30]3[CH2:34][O:33]C(C)(C)[O:31]3)=[C:18]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:17]=2)([CH3:14])[CH3:13])[CH:8]=[C:7]([C:41]([CH3:44])([CH3:43])[CH3:42])[C:6]=1[OH:45])([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[K+]>CO>[C:22]([C:20]1[CH:21]=[C:16]([S:15][C:12]([S:11][C:9]2[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:45])=[C:7]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:8]=2)([CH3:14])[CH3:13])[CH:17]=[C:18]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:19]=1[O:26][CH2:27][CH2:28][CH2:29][C@H:30]([OH:31])[CH2:34][OH:33])([CH3:25])([CH3:24])[CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86602765HCID 86602765, Verbindung

Produkt 1

HCID 58593383HCID 58593383, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 2,6-di-tert-butyl-4-(1-{3,5-di-tert-butyl-4-[3-(2,2-dimethyl-[1,3]dioxo-lan-4(R)-yl)-propoxy]-phenylsulfanyl}-1-methyl-ethylsulfanyl)-phenol (Ex-11, 230 mg, 0.35 mmol) in 20 ml MeOH, was added 1.0 N HCl dropwise until the mixture turned cloudy. Then small amount of MeOH was added to the mixture until it became clear. The mixture was stirred at room temperature, and HPLC indicated that the reaction completed within 2 hours. The mixture was neutralized with 5N KOH and extracted with EtOAc. The combined organic phase was washed with water, dried over MgSO4, and concentrated to dryness. The residue was purified by silica gel column chromatography to give 0.2 g (93%) 5-{2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenoxy}-pentane-1,2(S)-diol as a white solid, mp 68–71° C. 1H-NMR (CDCl3) δ 7.53 (s, 2H), 7.45 (s, 2H), 5.36(s, 1H), 3.67–3.79 (m, 4H), 3.46–3.52 (m, 1H), 1.91–2.17 (m, 4H), 1.42–1.45 (m, 42H). MS m/z: 636.4119 ([M+NH4]+, 20%). Anal. calcd for C36H58O4S2: C, 69.86; H, 9.44; S, 10.36; found: C, 70.10; H, 9.15, S, 10.13.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-24b73eed2dfb45738b37a0c49932c614
Quelldatensatz
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07271274B2

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