Hydrochloric Acid → HCID 13721779, compound

HRID 1608080Notes

Reaction equation

HRID 1608080 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 1octynyllithium (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. 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-490c26bd1b6f4fbf8c18cc4b4a5c9ce5
Source dataset
uspto-grants-1989_09
Patent number
US04868337

Reaction notes

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