Diethyl Malonate → 11-[(3S,4S)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoic acid

HRID 398080Notes

Reaction equation

HRID 398080 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C@@H:7]([CH2:22]C=C)[C@:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1.[F:25][C:26]([F:48])([C:44]([F:47])([F:46])[F:45])[CH2:27][CH2:28][CH2:29][CH:30]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH:42]=[CH2:43])[C:31]([O:33]CC)=[O:32].ICCCC(F)(F)C(F)(F)F.C(OCC)(=O)CC(OCC)=O.ICCCCCCC=C>>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C@@H:7]([CH2:22][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH:30]([CH2:29][CH2:28][CH2:27][C:26]([F:25])([F:48])[C:44]([F:45])([F:46])[F:47])[C:31]([OH:33])=[O:32])[C@:8]([C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 7761Diethyl MalonateHCID 120170571,1,1,2,2-Pentafluoro-5-iodopentaneHCID 12043773(3S,4S)-7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-(2-propenyl)thiochromanHCID 12043786Ethyl 2-(4,4,5,5,5-pentafluoropentyl)-9-decenoateHCID 138898108-Iodooct-1-ene

Product 1

HCID 1204377711-[(3S,4S)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoic acid

Procedure

Starting with the (3S,4S)-7-methoxy-3-(4-methoxy-phenyl)-3-methyl-4-(2-propenyl)thiochroman prepared in Example 3 and ethyl 2-(4,4,5,5,5-pentafluoropentyl)-9-decenoate separately prepared from 1-iodo-4,4,5,5,5-pentafluoropentane, diethyl malonate and 1-iodo-7-octene, a procedure analogous to that as shown in Example 2 or 3 was repeated to give 11-[(3S,4S)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoic acid.

Sources & evidence

ORD record
ord-c83e5b35dddb43bea1c9570b6147f161
Source dataset
uspto-grants-2003_08
Patent number
US06610733B2

Reaction notes

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