Methane, dichloromethoxy- → 6-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalene-2-carbaldehyde

HRID 2404199ノート

反応式

HRID 2404199 の反応式
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]([CH3:22])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.[CH3:28][O:29]C(Cl)Cl>ClCCCl.ClCCl>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([O:11][C:12]2[CH:21]=[C:20]3[C:15](=[C:14]([CH3:22])[CH:13]=2)[CH:16]=[C:17]([CH:28]=[O:29])[CH:18]=[CH:19]3)[CH2:9][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 681727973-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthalene

生成物 1

HCID 866684296-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalene-2-carbaldehyde収率 98.6%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a mixture of 3-(4-tert-butyl-cyclohexyloxy)-1-methyl-naphthalene (450 mg, 1.5 mmol) in 1,2-dichloroethane (9 mL) was added tin tetrachloride (236 uL, 2 mmol) at 0° C. After stirred at 0° C. for 1 hr, dichloromethyl methyl ether (183 uL, 2 mmol) was added. The solution was stirred at 0° C. for 1 hr and then warmed to room temperature. The mixture was added ice water and stirred for 1 hr, then the dark solution was diluted with dichloromethane and washed with water. The organic phase was washed with sodium bicarbonate aqueous, and dried over MgSO4. The drying agent was filtered off and the solvent was concentrated to dryness to give dark solid product (0.48 g, yield: 97%). ESI-MS: 325.20 (M+H)+.

後処理

  1. stirringThe solution was stirred at 0° C. for 1 hr
  2. temperaturewarmed to room temperature
  3. stirringstirred for 1 hr
  4. washwashed with water
  5. washThe organic phase was washed with sodium bicarbonate aqueous
  6. dry with materialdried over MgSO4
  7. filtrationThe drying agent was filtered off
  8. concentrationthe solvent was concentrated to dryness

出典と根拠

ORDレコード
ord-c4eff4b594a346c0a18c8160f707311f
出典データセット
uspto-grants-2014_08
特許番号
US08802659B2

反応ノート

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