(Cyclohex-1-en-1-yl)methanol → Methyl 5-chloro-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzoate

HRID 1849917Notes

Reaction equation

HRID 1849917 reaction equation
[C:1]1(CO)CCCCC=1.[Cl:9][C:10]1[C:11]([O:21][CH:22]2[CH2:27][CH2:26][C:25](=[CH2:28])[CH2:24][CH2:23]2)=[CH:12][C:13]([F:20])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16]>>[Cl:9][C:10]1[C:11]([O:21][CH:22]2[CH2:27][CH2:26][C:25]3([CH2:1][CH2:28]3)[CH2:24][CH2:23]2)=[CH:12][C:13]([F:20])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 317542(Cyclohex-1-en-1-yl)methanolHCID 86703796Methyl 5-chloro-2-fluoro-4-((4-methylenecyclohexyl)oxy)benzoate

Product 1

HCID 86703797Methyl 5-chloro-2-fluoro-4-(spiro[2.5]octan-6-yloxy)benzoate

Procedure

Following the procedure as described in Example 342 Step 2 and making non-critical variations to replace cyclohexenylmethanol with methyl 5-chloro-2-fluoro-4-((4-methylenecyclohexyl)oxy)benzoate, the title compound was obtained as a colorless syrup (0.769 g, 85% yield): 1H NMR (300 MHz, CDCl3) δ 7.95 (d, J=7.7 Hz, 1H), 6.68 (d, J=12.4 Hz, 1H), 4.49-4.41 (m, 1H), 3.88 (s, 3H), 1.99-1.78 (m, 4H), 1.53-1.32 (m, 4H), 0.33-0.27 (m, 4H).

Sources & evidence

ORD record
ord-bda0b872a6fd41148b74eadb74646805
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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