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D-Psicose → Methyl 6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-carboxylate

HRID 1643661
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HRID 1643661 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([OH:17])[C:8](Br)=[C:9]2[O:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10]=12)=[O:4].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([OH:17])[CH:8]=[C:9]2[O:13][C:12]([CH3:14])([CH3:15])[CH2:11][C:10]=12)=[O:4]
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참가 물질

5

반응물 2

HCID 441036D-PsicoseHCID 595601447-Bromo-6-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

생성물 1

HCID 59560026Methyl 6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-carboxylate수율 81%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A suspension of 7-bromo-6-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester (197d) (52 g, 0.17 mol) and 10% Pd on Carbon (5 g) in MeOH (1 L) was stirred under 50 Psi of H2 at 35-40° C. for 3 days. After HPLC indicated complete consumption of 197d, the reaction mixture was filtered through Celite and the filtrate was concentrated to give the title compound (30.6 g, 79.6%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 6.93 (s, 1H), 6.39 (s, 1H), 5.32 (s, 1H), 3.81 (s, 3H), 3.17 (s, 2 H), 1.40 (s, 6H).

후처리

  1. customconsumption of 197d
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-12221676189748aba884fb57637f5ab6
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08119624B2

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