Isobutyraldehyde → 1-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-ol

HRID 460282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460282
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[Li]CCCC.[CH:18](=[O:22])[CH:19]([CH3:21])[CH3:20].[Cl-].[NH4+]>C1COCC1>[CH3:10][C:7]1([CH3:11])[C:6]2[CH:12]=[C:2]([CH:18]([OH:22])[CH:19]([CH3:21])[CH3:20])[CH:3]=[CH:4][C:5]=2[O:9][CH2:8]1

Komponenten

6

Edukt 4

HCID 6561IsobutyraldehydeHCID 25517Ammonium ChlorideHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuranHCID 178418339Butyllithium

Produkt 1

HCID 220414081-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-olAusbeute 106,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (2.03 g, 8.93 mmol) in dry THF (10 mL) at −78° C., under argon, was added dropwise n-BuLi (1.6 M in hexane, 13.4 mmol, 8.38 mL). The mixture was stirred for 5 minutes then isobutyraldehyde (1.22 mL, 8.38 mmol) was added and the mixture was slowly warmed up to room temperature and stirred overnight at room temperature. Aqueous ammonium chloride was added and the solution extracted with ethylacetate and the organic extract was dried (MgSO4), filtered and evaporated. The residue was purified on silica gel (0% to 20% ethyl acetate in hexane) to give 1.97 g of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2 -methyl-propan-1-o1(100%). 1H NMR (300 MHz; CDC13): δ0.77(d, J=6.6 Hz, 3H), 0.90 (d, J=6.6 Hz, 3H), 1.33 (s, 6H), 1.95 (m, 1H), 4.23 (s, 2H), 4.28 (d, J=7.2 Hz, 2H), 6.72 (d, J=8.4 Hz, 1H), 7.03 (dd, J=8.1 Hz and 1.8 Hz, 1H), 7.06 (d, J=1.5 Hz, 1H).

Aufarbeitung

  1. stirringstirred overnight at room temperature
  2. extractionthe solution extracted with ethylacetate
  3. extractionthe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on silica gel (0% to 20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5e127a92d5db41669a4b73559435c092
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196108B2

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