Water → N-(3-Methyl-5-methylene-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

HRID 718812Notes

Reaction equation

HRID 718812 reaction equation
[CH3:1]C([O-])(C)C.[K+].C1COCC1.[CH3:12][C:13]1[C:14]([NH:24][C:25](=[O:27])[CH3:26])=[CH:15][C:16]2[CH2:17][CH2:18][CH2:19][C:20](=O)[C:21]=2[CH:22]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH3:12][C:13]1[C:14]([NH:24][C:25](=[O:27])[CH3:26])=[CH:15][C:16]2[CH2:17][CH2:18][CH2:19][C:20](=[CH2:1])[C:21]=2[CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 20222994N-(3-Methyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 86722422N-(3-Methyl-5-methylene-5,6,7,8-tetrahydronaphthalen-2-yl)acetamideYield 60.2%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

In a mechanically stirred 50 L vessel, Et2O (12.5 L) was added to methyltriphenylphosphonium bromide (1.81 kg, 5.06 mol). KOtBu (566 g, 5.06 mol) was added. The mixture was heated to reflux for about 1 h. THF (5 L) was added followed by addition of N-(3-methyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (75) (475 g, 2.19 mol). The mixture was warmed to reflux overnight. The reaction was diluted with Et2O (5 L). The resulting mixture was cooled to rt and then poured into water (30 L). After stirring for about 1 h at rt, the layers were left standing to separate. The aqueous layer was removed and the organic mixture was filtered rinsing with Et2O. The solids were dried in vacuo to afford N-(3-methyl-5-methylene-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (76) (284 g, 60% yield). 1H NMR (300 MHz, DMSO): δ 9.24 (s, 1H), 7.49 (s, 1H), 7.24 (s, 1H), 5.48 (m, 1H), 4.86 (m, 1H), 2.65 (m, 2H), 2.49 (m, 2H), 2.35 (s, 3H), 2.06 (s, 3H), 1.75 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for about 1 h
  3. temperatureThe mixture was warmed
  4. temperatureto reflux overnight
  5. waitthe layers were left
  6. customto separate
  7. customThe aqueous layer was removed
  8. filtrationthe organic mixture was filtered
  9. washrinsing with Et2O
  10. customThe solids were dried in vacuo

Sources & evidence

ORD record
ord-62b02290691f4e14935fa65c24ae17e7
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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