Hexane → HCID 17932014、化合物

HRID 2174323ノート

反応式

HRID 2174323 の反応式
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH:12]([Br:16])[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C(=N)O[C:22]([CH3:25])([CH3:24])[CH3:23].CN(C)C(=O)C.CCCCCC>C(Cl)(Cl)Cl.C1CCCCC1.B(F)(F)F.CCOCC>[C:22]([O:14][C:13](=[O:15])[CH:12]([Br:16])[CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:17])([CH3:25])([CH3:24])[CH3:23]

参加物

8

反応物 4

HCID 8058HexaneHCID 31374DimethylacetamideHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 21197492HCID 21197492、化合物

生成物 1

HCID 17932014HCID 17932014、化合物収率 79.1%

試薬・触媒・溶媒 3

HCID 8000Boron trifluoride etherate触媒HCID 6212Chloroform溶媒HCID 8078Cyclohexane溶媒

実験手順

To a solution of α-bromoglutaric acid-5-benzylester (See Example 18a(i)(a); 1.2 g, 4.0 mmol) in chloroform (Merck, 5 mL) a solution of tert-butyl 2,2,2-trichloroacetimidate (Fluka, 1.57 mL, 8.52 mmol) in cyclohexane (Merck, 5 mL) was added dropwise over 5 minutes. N,N-Dimethylacetamide (Fluka, 0.88 mL) was added followed by boron trifluoride ethyl etherate (Aldrich, 80 μL) as catalyst. The reaction mixture was stirred for 5 days at room temperature. Hexane was added and the organic phase washed with brine three times, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified using normal phase chromatography (Silica column (40 g), solvents: A=hexane, B=ethyl acetate, gradient: 10 to 35% B over 15 min, flow rate 40 mL/min, UV detection at 214 and 254 nm) affording 1.13 g (79%) of the pure product. Structure was verified by NMR

後処理

  1. washthe organic phase washed with brine three times
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product was purified
  5. waitA=hexane, B=ethyl acetate, gradient: 10 to 35% B over 15 min

出典と根拠

ORDレコード
ord-05082266f0714dfaa634dbb968f0fe93
出典データセット
uspto-grants-2015_06
特許番号
US09061080B2

反応ノート

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