Hydrochloric Acid → Methyl(phenylethynyl)isopropoxyborane

HRID 1608081Notes

Reaction equation

HRID 1608081 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, 3H); 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. Anal. Calcd. for C12H15BO: C, 77.46; H, 8.13. Found: C, 76.00; H, 7.69.

Workup

  1. customVolatiles were removed under reduced pressure at ambient temperature

Sources & evidence

ORD record
ord-514919e829ed4f52b01f3e74b9155aaa
Source dataset
uspto-grants-1989_09
Patent number
US04868337

Reaction notes

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