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

HRID 713978노트

반응식

HRID 713978 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-e9064b839b2a430e92b74b9e33e47eb8
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186367B2

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