Hydrochloric Acid → HCID 14438344, compound

HRID 1608079Notes

Reaction equation

HRID 1608079 reaction equation
[CH:1]([B:5]([O:10][CH:11]([CH3:13])[CH3:12])OC(C)C)([CH2:3][CH3:4])[CH3:2].[C:14]([Li])#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].Cl.[B].C=C(C)C>C(OCC)C>[CH:1]([B:5]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[O:10][CH:11]([CH3:12])[CH3:13])([CH2:3][CH3:4])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8255IsobutyleneHCID 5462311BoronHCID 13183021Boronic acid, (1-methylpropyl)-, bis(1-methylethyl) esterHCID 178506802HCID 178506802, compound

Product 1

HCID 14438344HCID 14438344, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

sec-Butyl(1-octynyl)isopropoxyborane was prepared following the method of Example 12 with sec-butyldiisopropoxyborane (10.79 g, 58 mmol) in ethyl ether (58 mL) and added to a solution of 1-octynyllithium (64 mmol in 64 mL, THF) and quenched with HCl in ethyl ether (18.82 mL, 64 mmol). Yield: 10.1 g (74%), bp 68°-70° C. (0.1 mm Hg); n20D 1.4366; proton NMR (CDCl3)δ4.60 (septet, =18 Hz, 1H), 2.23 (triplet, 2H), 1.17 (d, J=18 Hz, 6H), 0.87 (m, 9H); boron NMR (CDCl3)δ+41.6 ppm(s); mass spectrum (chemical ionization, isobutene) m/e 237 M+H, 15%); IR (thin film) 2183, 1324 cm-1. Anal Calcd. for C15H29BO: C, 76.77; H, 12.38; B, 4.58. Found: C, 76.30; H, 12.39; B, 4.63.

Sources & evidence

ORD record
ord-5ea1afc5479d48ba9728aafe781de0aa
Source dataset
uspto-grants-1989_09
Patent number
US04868337

Reaction notes

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