Hydroxyphenylacetic acid → 3,3,3-Triphenylpropyl 2-(4-hydroxyphenyl)acetate

HRID 263807ノート

反応式

HRID 263807 の反応式
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](O)=[O:32])=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[OH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:10][CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:32])=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 127Hydroxyphenylacetic acidHCID 11776TriphenylphosphineHCID 2986573,3,3-Triphenylpropan-1-olHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 537496193,3,3-Triphenylpropyl 2-(4-hydroxyphenyl)acetate収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To triphenylpropanol (3.98 mmol), 4-hydroxyphenylacetic acid (3.98 mmol), and triphenylphosphine (4.39 mmol) in dry THF (20 mL) at 0° C. under a nitrogen atmosphere, was added DEAD (4.39 mmol) in dry THF (20 mL) over 15 minutes. The reaction was stirred at room temperature for 16 h and then the THF was evaporated. The residue was chromatographed on silica gel using 15-30% EtOAc/hexanes. White solid, mp=136°-138° C. (ether), 34% yield. 1H NMR δ 7.15-7.27 (m, 15H), 7.10 (d, J=8.5 Hz, 2H), 6.77 (d, J=8.5 Hz, 2H), 4.90 (s, 1H), 3.90 (t, J=7.9 Hz, 2H), 3.47 (s, 2H), 2.93 (t, J=7.9 Hz, 2H). Anal. calcd. for C29H26O3 : C, 82.44; H, 6.20. Found: C, 82.29; H, 6.24.

後処理

  1. customthe THF was evaporated
  2. customThe residue was chromatographed on silica gel using 15-30% EtOAc/hexanes

出典と根拠

ORDレコード
ord-d9bfded6615342a1bfb8213e25ec4660
出典データセット
uspto-grants-1997_07
特許番号
US05643950

反応ノート

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