Tetrahydrofuran → HCID 22978424、化合物

HRID 1860681ノート

反応式

HRID 1860681 の反応式
[CH:1]([Mg]Br)=[CH2:2].O1CC[CH2:7][CH2:6]1.O1CCCC1.C(O[C:18](=[O:33])[C:19]([C:31]#[N:32])=[C:20]([CH3:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)C.Cl.[OH2:35]>[I].[Cu].C(OCC)C>[CH2:6]([O:35][C:18](=[O:33])[CH:19]([C:31]#[N:32])[C:20]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)([CH3:30])[CH:1]=[CH2:2])[CH3:7]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 21885828Hydrate;hydrochlorideHCID 600747842-Cyano-4-(4-methoxy-phenyl)-3-methyl-but-2-enoic Acid Ethyl EsterHCID 178420667HCID 178420667、化合物

生成物 1

HCID 22978424HCID 22978424、化合物

試薬・触媒・溶媒 2

HCID 178505378HCID 178505378、化合物触媒HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 1 M vinyl magnesium bromide/tetrahydrofuran (38.6 ml), copper iodine (0.08 g), and tetrahydrofuran (50 ml) was added the solution of product produced in STEP 1 (10.0 g) and ethyl ether (20 ml). The resulting solution was stirred at room temperature overnight. The solution was poured into 5% hydrochloric acid/water (100 ml). The organic layer was separated and the aqueous portion was extracted well with ethyl ether and the combined organic extract was washed with water, brine and dried over MgSO4. The crude product was purified on a silica gel column, eluting with 10% ethyl acetate/hexane to afford light yellow oil (6.3 g). The 1H NMR was consistent with the proposed structure.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous portion was extracted well with ethyl ether
  3. extractionthe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over MgSO4
  6. customThe crude product was purified on a silica gel column
  7. washeluting with 10% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-15853ae3ea9a453d8481626b2461b191
出典データセット
uspto-grants-2003_03
特許番号
US06531494B1

反応ノート

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