3-Hydroxymethyl-4-(3-thienyl)-7-hydroxy-2-naphthoic acid → 3-Hydroxymethyl-4-(3-furyl)-7-hydroxy-2-naphthoic acid

HRID 22411Notes

Reaction equation

HRID 22411 reaction equation
[OH:1][C:2]1[C:3]([C:19]([OH:21])=[O:20])=[C:4]([CH3:18])[C:5]2[C:10]([C:11]=1[C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)=[CH:9][CH:8]=[C:7]([OH:17])[CH:6]=2.[OH:22][CH2:23]C1C(C(O)=O)=CC2C(C=1C1C=CSC=1)=CC=C(O)C=2>>[OH:22][CH2:23][C:2]1[C:3]([C:19]([OH:21])=[O:20])=[CH:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)=[CH:9][CH:8]=[C:7]([OH:17])[CH:6]=2.[OH:1][C:2]1[C:3]([C:19]([OH:21])=[O:20])=[C:4]([CH3:18])[C:5]2[C:10]([C:11]=1[C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)=[CH:9][CH:8]=[C:7]([OH:17])[CH:6]=2

Participants

4

Reactant 2

HCID 199302453-Hydroxymethyl-4-(3-thienyl)-7-hydroxy-2-naphthoic acidHCID 678099503-Hydroxy-methyl-4-(3-furyl)-7-hydroxy-2-naphthoic acid

Product 2

HCID 199302263-Hydroxymethyl-4-(3-furyl)-7-hydroxy-2-naphthoic acidHCID 678099503-Hydroxy-methyl-4-(3-furyl)-7-hydroxy-2-naphthoic acid

Procedure

Following the procedure described in Example 7, but substituting (1S,5R) 3-[3-(3α-hydroxy-6,8-dioxabicyclo[3.2.1]octanyl)]benzyl alcohol (Alcohol 3) for 5-[4-(4-hydroxy)tetrahydropyranyl]pyridin-3-ylmethanol (Alcohol 1), and substituting 3-hydroxymethyl-4-(3-thienyl)-7-hydroxy-2-naphthoic acid, lactone form (Lactone 4), for 3-hydroxymethyl-4-(3-furyl)-7-hydroxy-2-naphthoic acid, lactone form (Lactone 1), the title compound was obtained as a solid; m.p. 221°-222° C.

Sources & evidence

ORD record
ord-abe1c194189e4931a9a4594b9c949bc7
Source dataset
uspto-grants-1995_06
Patent number
US05428060

Reaction notes

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