Ammonium formate → HCID 59300426, compound

HRID 603368Notes

Reaction equation

C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6]/[C:7]/2=[CH:12]\[C:13]([O:15][CH2:16][CH3:17])=[O:14].C([O-])=O.[NH4+]>CCO>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH:7]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 65 °C

Procedure

A round bottomed flask was flushed with argon and then charged with Pd(OH)2 (316 mg, 10 wt %). The flask was evacuated and back-filled with argon, and then EtOH (5 mL) was added to the catalyst. Ethyl (2E)-(4-methoxy-2,3-dihydro-1H-inden-1-ylidene)ethanoate (Example 8, 3.2 g, 13.6 mmol) was added as a solution in EtOH (63 mL). Ammonium formate (4.3 g, 68 mmol) was added, and the reaction mixture was heated to 65° C. After 2 h, the reaction mixture was cooled and filtered through a pad of Celite®, and concentrated under reduced pressure. The reaction mixture was used without further purification according to the method outlined in Example 6 to give the title compound (2.3 g, 78%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.14 (t, 1H), 6.76 (d, 1H), 6.67 (d, 1H), 4.91 (br s, 1H), 4.19 (q, 2H), 3.60 (m, 1H), 2.85-2.88 (m, 1H), 2.76-2.80 (m, 2H), 2.19-2.26 (m, 2H), 1.76-1.82 (m, 1H), 1.26 (t, 3H); GC-MS m/z[M+H]+ 221.

Workup

customA round bottomed flask was flushed with argon
additioncharged with Pd(OH)2 (316 mg, 10 wt %)
customThe flask was evacuated
additionback-filled with argon
additionEtOH (5 mL) was added to the catalyst
temperaturethe reaction mixture was cooled
filtrationfiltered through a pad of Celite®
concentrationconcentrated under reduced pressure
customThe reaction mixture was used without further purification

Sources & evidence

ORD record: ord-308f2b7cd67449349a04be0c3ec240fc
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906653B2

Reaction notes

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