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

HRID 460282ノート

反応式

HRID 460282 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 220414081-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-ol収率 106.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5e127a92d5db41669a4b73559435c092
出典データセット
uspto-grants-2007_03
特許番号
US07196108B2

反応ノート

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