Allyltributylstannane → 5-allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one

HRID 1582237노트

반응식

HRID 1582237 반응식
[CH3:1][C:2]1([CH3:20])[O:7][C:6](=[O:8])[C:5]2[C:9](S(C(F)(F)F)(=O)=O)=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1.[Li+].[Cl-].[CH2:23]([Sn](CCCC)(CCCC)CCCC)[CH:24]=[CH2:25].[F-].[K+]>CC1CNC(=O)C1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>[CH2:25]([C:9]1[C:5]2[C:6](=[O:8])[O:7][C:2]([CH3:20])([CH3:1])[O:3][C:4]=2[CH:12]=[CH:11][CH:10]=1)[CH:24]=[CH2:23]

참가 물질

8

반응물 4

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 22336191HCID 22336191, 화합물

생성물 1

HCID 111486725-allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one수율 97.2%

시약·촉매·용매 3

HCID 521585Tris(furan-2-yl)phosphane촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 5339204-Methyl-2-pyrrolidinone용매

실험 절차

To a stirred suspension of 2,2-dimethyl-5-(trifluoromethanesulfonyl)benzo[1,3]dioxin-4-one (iii) (2.0 g, 6.13 mmol), anhydrous LiCl (0.8 g, 18.4 mmol), Pd2(dba)3 (112 mg, 0.12 mmol), and tri-(2-furyl)phosphine (115 mg, 0.49 mmol) in 4-methyl-2-pyrrolidinone (10 mL) was added allyltributyltin (2.35 mL, 7.36 mmol). After stirring for 48 h at rt, saturated aqueous KF (20 mL) was added and an extraction was performed with Et2O (3×). The combined organics were dried over MgSO4, concentrated in vacuo and the residue was purified by FC (4% EtOAc/hexanes) to give 1.3 g of 5-allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one (iv) which was slightly impure.

후처리

  1. extractionan extraction
  2. dry with materialThe combined organics were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by FC (4% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-232c9d3ec92b40cc98b4b7cf8096c00e
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734209B2

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