Mercaptoethanesulfonic acid → 1,1,4,4-Tetramethyltetralin

HRID 1781216

Reaktionsgleichung

Reaktionsgleichung von HRID 1781216
BrCC([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]2([CH3:18])[CH3:17])=O.SCCS(O)(=O)=O.[Na:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C1COCC1.O.C(OCC)(=O)C>[Na:26].[CH3:17][C:8]1([CH3:18])[C:7]2[C:12](=[CH:13][CH:14]=[CH:5][CH:6]=2)[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9]1

Komponenten

10

Edukt 4

HCID 598Mercaptoethanesulfonic acidHCID 11430Potassium CarbonateHCID 28013372-Bromo-1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-oneHCID 5360545Sodium

Produkt 2

HCID 811861,1,4,4-TetramethyltetralinHCID 5360545Sodium

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-(bromoacetyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (12) (15.5 mg, 0.050 mmol) in DMF (0.13 mL) and THF (0.13 mL) was added a freshly prepared solution of 2-mercapto-1-ethanesulfonic acid, sodium salt (2) (25 mg, 0.15 mmol) and potassium carbonate (21 mg, 0.15 mmol) in water (0.15 mL) at room temperature. The resulting biphasic mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate (2.5 mL), and the organic layer was separated, washed with water (2×1 mL) and brine (1×1 mL), dried and concentrated to afford 6-[2'-mercapto-1'-ethanesulfonic acid, sodium salt)acetyl]-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (20) as a solid. 1H NMR (pyr-d5): δ 8.19, 7.90, 7.40 (m, 3H), 4.11 (s, 2H), 3.5 (m, 4H), 1.55 (s, 4H), 1.20 (d, 12H).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with water (2×1 mL) and brine (1×1 mL)
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bd07e98aceef4b509d4e39b6ba9624c9
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05632898

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