1-Bromooctadecane → HCID 18705578, compound

HRID 363399Notes

Reaction equation

HRID 363399 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]>C(OCC)(=O)C.O.CN1C(=O)N(C)CCC1.C1COCC1>[C:8]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:6][CH:5]([CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH3:32])[C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 3

HCID 82181-BromooctadecaneHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 18705578HCID 18705578, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of N-(diphenylmethylene)-glycine ethyl ester (67.3 g, 0.250 mol) in a 1:1 mixture of anhydrous THF (500 ml) and DMPU (500 ml) at -78° C. under a dry argon atmosphere was added a solution of lithium bis(trimethylsilyl)amide (250 ml--1.0M in THF, 0.25 mol) over a 10 min period. The resulting orange solution was stirred for 1.5 h at -78° C. While maintaining the temperature at -78° C., a solution of 1-bromooctadecane (83.4 g, 0.250 mol) in a 1:1 mixture of anhydrous THF (250 ml) and DMPU (250 ml) was added over a 10 min period and the resulting mixture was allowed to warm to room temperature. After stirring the mixture for 17 h, H2O (50 ml) and then ethyl acetate (2 l) were added. The solution was washed with H2O (4×2 l). The solution was dried over Na2CO3 -Na2SO4 and the volume was reduced in vacuo to 1 l. The product was crystallized by the addition of hexane to give 104 g (80% yield) of an off-white crystalline solid: mp 62°-5° C.; 1H NMR (CDCl3) δ 0.88 (t, J =6.6 Hz, 3 H), 1.27 (m, 35 H), 1.90 (m, 2 H), 4.03 (m, 1 H), 4.17 (m, 2 H), 7.17 (m, 2 H), 7.36 (m, 6 H), 7.64 (m, 2 H).

Workup

  1. temperatureWhile maintaining the temperature at -78° C.
  2. additionwas added over a 10 min period
  3. temperatureto warm to room temperature
  4. stirringAfter stirring the mixture for 17 h
  5. washThe solution was washed with H2O (4×2 l)
  6. dry with materialThe solution was dried over Na2CO3 -Na2SO4
  7. customThe product was crystallized by the addition of hexane

Sources & evidence

ORD record
ord-7eee34a9394347d88e933f3bac1dffc9
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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