Hydrochloric Acid → Phenyl(1-hexynyl)isopropoxyborane

HRID 2291366노트

반응식

HRID 2291366 반응식
[C:1]([Li])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C#CCCCC.C([Li])CCC.[C:19]1([B:25](OC(C)C)[O:26][CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.[B].C=C(C)C>C(OCC)C>[C:6]1([B:25]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:26][CH:27]([CH3:28])[CH3:29])[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=1

참가 물질

9

반응물 7

HCID 313Hydrochloric AcidHCID 8255IsobutyleneHCID 127321-HexyneHCID 569210Bis(1-methylethyl) B-phenylboronateHCID 5462311BoronHCID 178418339ButyllithiumHCID 178506798HCID 178506798, 화합물

생성물 1

HCID 13721780Phenyl(1-hexynyl)isopropoxyborane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

The title compound was prepared following the method of Example 14, using 1-hexynyllithium (64 mmol) prepared from 1-hexyne and n-butyl lithium in ethyl ether (64 mL) and phenyldiisopropoxyborane (11.96 g, 58 mmol) dissolved in ethyl ether (60 mL) and quenched with hydrogen chloride in ethyl ether (18.7 mL, 64 mmol). Yield. 11.2 g (86%), bp 102°-105° C. (0.4 mm Hg); n20D 1.5008; proton NMR (CDCl3) δ7.90 (m, 2H), 7.31 (m, 3H), 4.87 (septet, J=18 Hz, 1H), 2.33 (triplet, J=18 Hz, 2H), 1.23 (d, J=18 Hz, 6H), 0.90 (triplet, 3H); boron NMR (CDCl3) δ+36.5 ppm(s); mass spectrum (chemical ionization, isobutene) m/e 229 (M+H, 10%); IR (thin film) 2195, 1324 cm-1.

후처리

  1. customYield

출처 및 근거

ORD 기록
ord-0303d7f3447b44bca1daeb533ac66a80
출처 데이터셋
uspto-grants-1989_01
특허 번호
US04795821

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