Реакция #978

ord-a6be5895ebf2488a874923e3878acfbe

Уравнение реакции

C/C(C=O)=C\[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC1
aldehyde
C/C(C=O)=C\[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC1
(E)-3-[trans-(4-tert-Butyldimethylsilyloxycyclohexyl)]-2-methylprop-2-en-1-al
[Br][Mg][CH2]CCc1ccccc1
120
[Br][Mg][CH2]CCc1ccccc1
3-Phenyl-1-propylmagnesium bromide
OC(CCCc1ccccc1)CCCc1ccccc1
alcohol
OC(CCCc1ccccc1)CCCc1ccccc1
1,7-Diphenyl-4-heptanol
→
C/C(=C\[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC1)C(O)CCCc1ccccc1
alcohol
C/C(=C\[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC1)C(O)CCCc1ccccc1
(E)-1-[trans-(4-tert-Butyldimethylsilyloxycyclohexyl)]-2-methyl-6-phenylhex-1-en-3-ol

Реактанты

C/C(C=O)=C\[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC1
aldehyde
C/C(C=O)=C\[C@H]1CC[C@H](O[Si](C)(C)C(C)(C)C)CC1
(E)-3-[trans-(4-tert-Butyldimethylsilyloxycyclohexyl)]-2-methylprop-2-en-1-al
[Br][Mg][CH2]CCc1ccccc1
120
[Br][Mg][CH2]CCc1ccccc1
3-Phenyl-1-propylmagnesium bromide
OC(CCCc1ccccc1)CCCc1ccccc1
alcohol
OC(CCCc1ccccc1)CCCc1ccccc1
1,7-Diphenyl-4-heptanol

Реагенты

Нет

Растворители

C1CCOC1
THF

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

The alcohol 137 was prepared from the crude aldehyde 136. and 1.5 mL (0.75 mmol) of 120 in 2.0 mL of THF as described above for the synthesis of alcohol 121 in Example 1 to give 220 mg of the crude diastereomeric alcohol 137. Flash chromatography (elution with 20% ethyl acetate in hexane) afforded 146 mg of the alcohol 137 as an oil. 1H NMR consistent with structure.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05723459uspto-grants-1998_03