Hydrochloric Acid → Methyl(phenylethynyl)isopropoxyborane

HRID 2291370Notes

Reaction equation

HRID 2291370 reaction equation
[CH3:1][B:2](OC(C)C)[O:3][CH:4]([CH3:6])[CH3:5].[C:11]1([C:17]#[C:18][Li])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(OCC)C>[CH3:1][B:2]([C:18]#[C:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[O:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3392711Dipropan-2-yl methylboronateHCID 178506790HCID 178506790, compound

Product 1

HCID 13721775Methyl(phenylethynyl)isopropoxyboraneYield 817.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The reaction was run following the method of Example 14 using methyldiisopropoxyborane (6.34 g, 44 mmol) in ethyl ether (44 mL) and phenylethynyllithium (4.9 mmol) in ethyl ether (50 mL), then quenched with hydrogen chloride (14.33 mL, 49 mmol). Volatiles were removed under reduced pressure at ambient temperature to yield 7.45 g (91%) of the title product; n20D 1.5290; proton NMR (CDCl3) δ7.23 (m, 5H), 4.73 (septet, J=18 Hz, 1H), 1.23 (d, J=18 Hz, 6H), 0.53 (bs, 3); boron NMR (EE) δ+40.2 ppm(s). Mass spectrum (chemical ionization, isobutene) m/e 187 (M+H, 6%); IR (thin film) 2178, 1326 cm-1.

Workup

  1. customVolatiles were removed under reduced pressure at ambient temperature

Sources & evidence

ORD record
ord-df117439463641968584b8911263dd39
Source dataset
uspto-grants-1989_01
Patent number
US04795821

Reaction notes

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