Chloromethyl Methyl Ether → HCID 59858077, 화합물

HRID 254238노트

반응식

HRID 254238 반응식
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1([CH3:22])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([OH:16])[CH:12]=2)[O:7]1.C(N(C(C)C)CC)(C)C.[CH3:33][O:34][CH2:35]Cl>C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1([CH3:22])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([O:16][CH2:33][O:34][CH3:35])[CH:12]=2)[O:7]1

참가 물질

6

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 11716671HCID 11716671, 화합물

생성물 1

HCID 59858077HCID 59858077, 화합물수율 74.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid methyl ester from Example 13 (400 mg, 1.27 mmol) and diisopropyl ethylamine (DIPEA) (0.90 ml, 5 mmol) in 4 mL of DCM was slowly added chloromethyl methyl ether (0.30 mL, 3.8 mmol) at room temperature. The reaction was left over night. After the completion of reaction shown by TLC, the mixture was poured into brine and the organic layer was separated and dried over MgSO4. After the removal of solvents the residue was purified through flash column chromatography on silica gel (25% of ethyl acetate in hexane) to afford 340 mg of 3-(6-methoxymethoxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid methyl ester. 1H-NMR (300 MHz, CDCl3) δ (ppm)): 6.25 (s, 1H), 4.29 (s, 1H), 3.63 (s, 3H), 3.48 (s, 1H), 3.40 (s, 1H), 2.66-2.64 (m, 2H), 2.47-2.43 (m, 2H), 1.83-1.50, (m, 12H) 1.18 (s, 3H).

후처리

  1. customat room temperature
  2. waitThe reaction was left over night
  3. customAfter the completion of reaction
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. customAfter the removal of solvents the residue
  7. customwas purified through flash column chromatography on silica gel (25% of ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-38264c46038d4f548a55323b3909c51a
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875607B2

반응 노트

불러오는 중…