3,3-Dimethylbutanoyl chloride → HCID 68709936, compound

HRID 1787388Notes

Reaction equation

HRID 1787388 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[C:15]([CH3:21])=[CH:16][C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][C:11]=2[CH3:22])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(C1C=CC(C2C3C(C)=CC(C)=C(C)C=3OC2C)=CC=1)(C)C.BrC1C(C)=C(C)C2OC(C)C(C3C=CC(C(C)C)=CC=3)C=2C=1C.C(NC1C(C)=C(C)C2OC(C)C(C3C=CC(C(C)C)=CC=3)C=2C=1C)C1C=CC=CC=1.C(C1C=CC(C2C3C(C)=C(N)C(C)=C(C)C=3OC2C)=CC=1)(C)C.C(CC(Cl)=O)(C)(C)C.C(C1C=CC(C2C3C(C)=C([NH:149][C:150](=[O:156])[CH2:151][C:152]([CH3:155])([CH3:154])[CH3:153])C(C)=C(C)C=3OC2C)=CC=1)(C)C>CCCCCC>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[C:14]3[C:15]([CH3:21])=[C:16]([NH:149][C:150](=[O:156])[CH2:151][C:152]([CH3:155])([CH3:154])[CH3:153])[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][C@H:11]2[CH3:22])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

9

Reactant 7

HCID 815143,3-Dimethylbutanoyl chlorideHCID 17817794HCID 17817794, compoundHCID 23113975HCID 23113975, compoundHCID 23114053HCID 23114053, compoundHCID 23114076HCID 23114076, compoundHCID 23114242HCID 23114242, compoundHCID 23114279HCID 23114279, compound

Product 1

HCID 68709936HCID 68709936, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using 3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-1-benzofuran obtained in Reference Example 347, a mixture of cis isomer and trans isomer (3:2) of 3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran was synthesized in the same manner as in Reference Example 199. Using the mixture as it is as the compound, a mixture of cis isomer and trans isomer of 5-bromo-3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran was obtained in the same manner as in Reference Example 23. Using the compound, a mixture of cis isomer and trans isomer of N-benzyl-(3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)amine was obtained in the same manner as in Reference Example 24. Using the compound, (3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)amine was synthesized in the same manner as in Reference Example 30. Using the compound and tert-butylacetyl chloride, a mixture of cis isomer and trans isomer of N-(3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide was obtained in the same manner as in Example 1. The compound was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to synthesize the title compound. Yield: 18%. Melting point: 143-144° C. (hexane)

Workup

  1. customobtained in Reference Example 347
  2. customwas synthesized in the same manner as in Reference Example 199
  3. customwas obtained in the same manner as in Reference Example 23
  4. customwas obtained in the same manner as in Reference Example 24
  5. customwas synthesized in the same manner as in Reference Example 30
  6. customwas obtained in the same manner as in Example 1
  7. customThe compound was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)
  8. customto synthesize the title compound

Sources & evidence

ORD record
ord-6dc3ca0a13854c11804e68d97016a881
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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