Trimethyl orthoformate → HCID 67519476、化合物

HRID 1296203ノート

反応式

HRID 1296203 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:33])[NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[CH:30]=[CH:29][C:28](C=O)=[CH:27][CH:26]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:46]([O:51][CH3:52])([O:49][CH3:50])OC>CO>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16](=[O:33])[NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[CH:26]=[CH:27][C:28]([CH:46]([O:49][CH3:50])[O:51][CH3:52])=[CH:29][CH:30]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86589748HCID 86589748、化合物

生成物 1

HCID 67519476HCID 67519476、化合物収率 93.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a vigorously stirred mixture of methanol (250 mL) containing aldehyde (S29) (17.0 g, 39.3 mmol) and p-toluenesulfonic acid monohydrate (0.75 g, 3.9 mmol) was added trimethyl orthoformate (17 mL, 160 mmol). After 1.5 h of moderate heating (flask equipped with short path to drive reaction forward), the reaction was quenched with a 1:1 mixture of saturated sodium bicarbonate and water (150 mL) and diluted with CH2Cl2 (200 mL). The aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give a pale yellow solid (17.5 g, 36.6 mmol, 93%) which was used without further purification. 1H NMR (400 MHz, d6-DMSO): δ 7.88 (d, 2H, J=7.7 Hz), 7.79 (t, 1H, J=5.9 Hz), 7.68 (d, 2H, J=7.3 Hz), 7.43–7.30 (m, 11H), 7.19 (d, 1H, J=7.0 Hz), 5.40 (s, 1H), 4.29 (d, 2H, J=7.0 Hz), 4.20 (t, 1H, J=7.0 Hz), 4.11 (d, 2H, J=5.9 Hz), 3.25 (s, 6H). FAB/MS: 502 (M+Na+).

後処理

  1. temperatureAfter 1.5 h of moderate heating
  2. custom(flask equipped with short path to drive reaction forward)
  3. customthe reaction was quenched with a 1:1 mixture of saturated sodium bicarbonate and water (150 mL)
  4. additiondiluted with CH2Cl2 (200 mL)
  5. extractionThe aqueous layer was extracted with CH2Cl2
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fff76343056f47bbaa70263b2b950346
出典データセット
uspto-grants-2007_07
特許番号
US07244853B2

反応ノート

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