Water → [3-(4-Formyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester

HRID 2036274ノート

反応式

HRID 2036274 の反応式
[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.[C:14]([O:18][C:19](=[O:25])[NH:20][CH2:21][CH2:22][CH2:23]Br)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:14]([O:18][C:19](=[O:25])[NH:20][CH2:21][CH2:22][CH2:23][O:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1)([CH3:17])([CH3:16])[CH3:15]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 130742081-Naphthalenecarboxaldehyde, 5,6,7,8-tetrahydro-4-hydroxy-

生成物 1

HCID 57828234[3-(4-Formyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester収率 59.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Hydroxy-5,6,7,8-tetrahydro-naphthalene-1-carbaldehyde (109, 4.6 g, 29.1 mmol) (3-Bromopropyl)-carbamic acid tert-butyl ester (110, 4.6 g, 32 mmol), and potassium carbonate (6.03 g, 43.7 mmol) were stirred in 140 mL of dry DMF over night. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water and brine., dried with magnesium sulfate, filtered, concentrated and purified by flash chromatography (0-30% EtOAc/hexane) to give crude product, which was recrystallized from EtOAc/Hexane to give 5.8 g of 111, [3-(4-formyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester.

後処理

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with material, dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-30% EtOAc/hexane)
  7. customto give crude product, which
  8. customwas recrystallized from EtOAc/Hexane

出典と根拠

ORDレコード
ord-24cc1b6dd8064adb8115f637b2873f69
出典データセット
uspto-grants-2013_11
特許番号
US08575176B2

反応ノート

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