Hydrochloric Acid → HCID 13721779, compound

HRID 2291369Notes

Reaction equation

HRID 2291369 reaction equation
[CH:1]1([B:6]([O:11][CH:12]([CH3:14])[CH3:13])OC(C)C)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:15]([Li])#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl.[B].C=C(C)C>C(OCC)C>[CH:1]1([B:6]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[O:11][CH:12]([CH3:13])[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8255IsobutyleneHCID 5462311BoronHCID 13201851HCID 13201851, compoundHCID 178506802HCID 178506802, compound

Product 1

HCID 13721779HCID 13721779, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Cyclopentyldiisopropoxyborane (2.33 g, 37 mmol) in ethyl ether (37 mL) was added to an ethereal solution of 1-octynyllithium (41 mmoL in 41 mL ethyl ether), then quenched with HCl in ethyl ether (12.0 mL, 41 mmol). Workup as described in Example 14 yielded 6.95 g (76%), bp 100°-102° C. (0.1 mm Hg); n20D 1.4557; proton NMR (CDCl3) δ4.63 (septet, J=18 Hz, 1H), 2.23 (triplet, 1H), 1.17 (d, J=18 Hz, 6H), 0.83 (triplet, 3H); boron NMR (EE) δ+41.2 ppm(s); mass spectrum (chemical ionization, isobutene) m/e 249 (M+H), 40%); IR (thin film) 2186, 1344 cm-1. Anal. Calcd. for C16H29BO: C, 77.42; H, 11.78. Found: C, 77.02; H, 11.92.

Workup

  1. customyielded 6.95 g (76%), bp 100°-102° C. (0.1 mm Hg)

Sources & evidence

ORD record
ord-420c8ec416a64037b58818e6bd25b821
Source dataset
uspto-grants-1989_01
Patent number
US04795821

Reaction notes

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