Water → (1E)-1-[(methyloxy)methylidene]-2,3-dihydro-1H-indene-4-carbonitrile

HRID 2173242Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl-].[CH3:12][O:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:35]1[C:43]2[CH:42]=[CH:41][CH:40]=[C:39]([C:44]#[N:45])[C:38]=2[CH2:37][CH2:36]1.O>C1COCC1>[CH3:12][O:13]/[CH:14]=[C:35]1\[CH2:36][CH2:37][C:38]2[C:39]([C:44]#[N:45])=[CH:40][CH:41]=[CH:42][C:43]\1=2

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium bis(trimethylsilyl)amide (2 mL, 4 mmol, 2M in THF) was added to a stirred suspension of (methoxy methyl)triphenylphosphonium chloride (1.47 g, 4.29 mmol) in dry THF (20 mL) at 0° C. for 35 min and a solution of 1-oxo-2,3-dihydro-1H-indene-4-carbonitrile (450 mg, 2.86 mmol) in THF (10 mL) added over 10 min. The mixture was stirred at 0° C. for 2 h and at room temperature for 1 h. Water was added and the mixture was partitioned between EtOAc and brine. The organic layer was dried and concentrated. The crude product was purified via prep-TLC (PE:EtOAc=10:1) to afford (1E)-1-[(methyloxy)methylidene]-2,3-dihydro-1H-indene-4-carbonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 8.00 (d, J=8.3 Hz, 0.4H), 7.42 (d, J=8.3 Hz, 0.6H), 7.30-7.40 (m, 1H), 7.18-7.22 (m, 1H), 6.70 (s, 0.6H), 6.22 (s, 0.4H), 3.72 (s, 3H), 3.15 (t, J=5.7 Hz, 2H), 2.70-2.82 (m, 2H).

Workup

customthe mixture was partitioned between EtOAc and brine
customThe organic layer was dried
concentrationconcentrated
customThe crude product was purified via prep-TLC (PE:EtOAc=10:1)

Sources & evidence

ORD record: ord-7fdb23d167c54aea8097d7fed8cc47d5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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