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

HRID 713978ノート

反応式

HRID 713978 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 driving 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 driving agent was filtered off
  8. concentrationthe solvent was concentrated to dryness

出典と根拠

ORDレコード
ord-e9064b839b2a430e92b74b9e33e47eb8
出典データセット
uspto-grants-2015_11
特許番号
US09186367B2

反応ノート

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