Phthalimide → 2-(2,3-Dihydro-benzofuran-2-ylmethyl)-isoindole-1,3-dione

HRID 216251

反応式

HRID 216251 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[CH2:10]O.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[CH2:10][N:16]1[C:12](=[O:22])[C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15]1=[O:17]

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2795428(2,3-Dihydro-1-benzofuran-2-yl)methanol

生成物 1

HCID 690694492-(2,3-Dihydro-benzofuran-2-ylmethyl)-isoindole-1,3-dione収率 116.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of (2,3-dihydro-benzofuran-2-yl)-methanol (1.65 g, 11 mmol), phthalimide (3.24 g, 22 mmol), and triphenylphosphine (5.77 g, 22 mmol) in THF (40 mL) is added diethyl azodicarboxylate (3.46 mL, 22 mmol) at −10° C., and the mixture is allowed to warm to room temperature. After 20 h at rt, the mixture is concentrated in vacuo, and the residue is chromatographed on SiO2 (40% EtOAc in heptane) to afford 2-(2,3-dihydro-benzofuran-2-ylmethyl)-isoindole-1,3-dione (3.58 g). LCMS: RT=2.64 minutes; MS: 280 (M+H).

後処理

  1. concentrationthe mixture is concentrated in vacuo
  2. customthe residue is chromatographed on SiO2 (40% EtOAc in heptane)

出典と根拠

ORDレコード
ord-2e0da6441e384680864f8779dcdc4dcc
出典データセット
uspto-grants-2012_06
特許番号
US08193183B2

関連ノート

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