Hydrochloric Acid → Phenyl(1-hexynyl)isopropoxyborane

HRID 1608077노트

반응식

HRID 1608077 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.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

8

반응물 6

HCID 313Hydrochloric AcidHCID 8255IsobutyleneHCID 127321-HexyneHCID 569210Bis(1-methylethyl) B-phenylboronateHCID 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); boro 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. Anal. Calcd. for C15H 21 BO: C, 78.97; H, 9.28. Found: C, 78.18; H, 9.27.

후처리

  1. customYield

출처 및 근거

ORD 기록
ord-16abfdfd42b6452c9b4422c19a3f61aa
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04868337

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