Triphenylphosphine → HCID 178445771, 화합물

HRID 2404136노트

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HRID 2404136 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5]2.[C:14]([C@@H:18]1[CH2:23][CH2:22][C@H:21](O)[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O.C1(C)C=CC=CC=1>[C:14]([C@H:18]1[CH2:23][CH2:22][C@H:21]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5]3)[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 45894766-Hydroxy-2-naphthonitrileHCID 5363146Diisopropyl azodicarboxylateHCID 178445811HCID 178445811, 화합물

생성물 1

HCID 178445771HCID 178445771, 화합물수율 146.4%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a vial charged with 6-hydroxy-2-naphthonitrile (3.38 g, 0.02 mol, 1.0 eq.), cis-4-tert-butylcyclohexanol (6.24 g, 0.04 mol, 2.0 eq.), PPh3 (10.5 g, 0.04 mol, 2.0 eq.) and toluene (20 mL), was added DIAD (12 mL, 0.06 mol, 3.0 eq.) under nitrogen atmosphere at r.t. and stirred for 15 h. Water was added and extracted with EtOAc. The organic layer was purified by silica gel chromatography (PE:EA=10:1) to give the title compound (9.0 g, 86%) as a slight yellow solid. EDI-MS (M+1)+: 308.0. 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 7.78-7.73 (m, 2H), 7.54 (dd, 1H), 7.22 (dd, 1H), 7.14 (s, 1H), 4.33-4.30 (m, 1H), 2.29-2.25 (m, 2H), 1.93-1.90 (m, 2H), 1.48-1.26 (m, 2H), 1.25-1.10 (m, 3H), 0.91 (s, 9H).

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was purified by silica gel chromatography (PE:EA=10:1)

출처 및 근거

ORD 기록
ord-c00fd199fa7d4b64b461b7feb25514ea
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802659B2

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