Water → HCID 58972229, compound

HRID 922070Notes

Reaction equation

I[CH2:2][CH2:3][CH2:4]/[C:5](/[CH3:21])=[CH:6]/[CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH3:16])[C:11]([CH3:17])=[C:10]([CH3:18])[C:9]=1[O:19][CH3:20].[C-:22]#[N:23].[Na+].O.CC(OC)(C)C>CN(C=O)C>[CH3:20][O:19][C:9]1[C:10]([CH3:18])=[C:11]([CH3:17])[C:12]([O:15][CH3:16])=[C:13]([CH3:14])[C:8]=1[CH2:7]/[CH:6]=[C:5](\[CH3:21])/[CH2:4][CH2:3][CH2:2][C:22]#[N:23]

Participants

Conditions

Temperature: 45 °C

Procedure

1-((E)-6-iodo-3-methylhex-2-enyl)-2,5-dimethoxy-3,4,6-trimethylbenzene (412 mg, 1.024 mmol) was combined with NaCN (247.7 mg) and dissolved in DMF (2 mL). The reaction was stirred for 25 h at 45° C. then cooled to room temperature. To the mixture was added H2O (10 mL) followed by MTBE (6 mL) and the layers separated. The aqueous phase was extracted into MTBE (4×6 mL) and the combined organics washed with H2O (2×5 mL) followed by saturated NaCl solution (2×5 mL) and dried over Na2SO4. The organics were concentrated to give (E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-enenitrile as a pale yellow oil, 306.4 mg (99.0%). 1H NMR (400 MHz, CDCl3) d 5.14 (t, J=6.4 Hz, 1H), 3.65 (s, 6H), 3.37 (d, J=6.8 Hz, 2H), 2.26 (t, J=7.2 Hz, 2H), 2.18 (s, 9H), 2.12 (t, J=7.2 Hz, 2H), 1.76 (m, 4H). 13C NMR (100 MHz, CDCl3) d 153.1, 152.6, 132.5, 131.0, 128.5, 128.0, 125.4, 119.7, 60.8, 60.1, 38.2, 38.2, 26.1, 23.5, 16.4, 15.9, 12.8, 12.7, 12.2.

Workup

temperaturethen cooled to room temperature
customthe layers separated
extractionThe aqueous phase was extracted into MTBE (4×6 mL)
washthe combined organics washed with H2O (2×5 mL)
dry with materialdried over Na2SO4
concentrationThe organics were concentrated

Sources & evidence

ORD record: ord-4caecba87ed445ad882bbe90b6f5b6f9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278085B2

Reaction notes

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