3-(1-(4-Fluorophenyl)cyclohexyl)propanoyl chloride → 2-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-7-vinyl-4,5-dihydronaphtho[1,2-d]oxazole

HRID 1506382Notes

Reaction equation

HRID 1506382 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16](Cl)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:19]([C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)/[C:27](=[N:31]/O)/[CH2:26][CH2:25][CH2:24]2)=[CH2:20]>ClC1C=CC=CC=1Cl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]3[O:17][C:26]4[CH2:25][CH2:24][C:23]5[C:28](=[CH:29][CH:30]=[C:21]([CH:19]=[CH2:20])[CH:22]=5)[C:27]=4[N:31]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 866698893-(1-(4-Fluorophenyl)cyclohexyl)propanoyl chlorideHCID 121012766(NE)-N-(6-ethenyl-3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine2×

Product 1

HCID 671707562-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-7-vinyl-4,5-dihydronaphtho[1,2-d]oxazoleYield 14.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

To a solution of 3-(1-(4-fluorophenyl)cyclohexyl)propanoyl chloride (Preparation 42B, 215 mg, 0.799 mmol) and 6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime (Intermediate 1, 224 mg, 1.199 mmol) in 1,2-dichlorobenzene (2 mL) was added 4-(dimethylamino)pyridine (6.15 mg, 0.050 mmol), and the mixture was microwaved at 180° C. for 10 mins. The mixture of was purified by Combiflash (silica gel, 24 g) eluting with 5:95 followed by 2:8 ethyl acetate-hexane to give the desired 2-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)-7-vinyl-4,5-dihydronaphtho[1,2-d]oxazole (47 mg, 14.6% yield) as an oil. LC/MS M+1=402.26.

Workup

  1. customthe mixture was microwaved at 180° C. for 10 mins
  2. additionThe mixture
  3. customof was purified by Combiflash (silica gel, 24 g)
  4. washeluting with 5:95

Sources & evidence

ORD record
ord-68ab1e70827d4d1899b704b580895c2c
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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