Veratryl alcohol → Methyl 4-(3,4-dimethoxybenzyloxy)-3-chlorobenzoate

HRID 2099958

반응식

HRID 2099958 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1O)[C:17]([O:19][CH3:20])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[CH2:11][O:12][C:23]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[Cl:13]

참가 물질

6

반응물 4

HCID 7118Veratryl alcoholHCID 11776TriphenylphosphineHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 57796893Methyl 4-(3,4-dimethoxybenzyloxy)-3-chlorobenzoate수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of (3,4-dimethoxyphenyl)methanol (6.0 g, 40 mmol) (Aldrich Chemical Co., Milwaukee, Wis.) and methyl 3-chloro-4-hydroxybenzoate (2.5 g, 13.5 mmol) (Lancaster Synthesis Ltd, Windham, N.H.) in THF (100 mL) was cooled to 0° C. and treated with triphenylphosphine (8.8 g, 33.5 mmol). A solution of diethylazodicarboxylate (5.3 mL, 33.5 mmol) in THF (50 mL) was added dropwise over 30 minutes. After the addition was complete, the reaction was warmed to room temperature and stirred for an additional 30 minutes, and then concentrated to orange oil. The crude reaction was applied directly to a silica column and flushed with hexanes. The desired product was eluted from the column using 25% EtOAc in Hexanes to afford 1A as a light yellow solid (2.5 g, 56%).

후처리

  1. additionAfter the addition
  2. concentrationconcentrated to orange oil
  3. customThe crude reaction
  4. customflushed with hexanes
  5. washThe desired product was eluted from the column

출처 및 근거

ORD 기록
ord-d1f4d470a1d74677a7686f33a9dd5b5f
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569725B2

연결된 노트

불러오는 중…