Tert-butyl 6-bromohexanoate → 3-{3-[3-(5-tert-butoxycarbonylpentyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic Acid

HRID 988038Notes

Reaction equation

HRID 988038 reaction equation
[OH:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][C:26]([O:28]CC)=[O:27])[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>>[C:40]([O:39][C:37]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][O:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])[CH:19]=[CH:20][C:21]=2[O:22][CH3:23])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

3

Reactant 2

HCID 11550568Tert-butyl 6-bromohexanoateHCID 69792380Ethyl 3-[3-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl)acrylate

Product 1

HCID 697924123-{3-[3-(5-tert-butoxycarbonylpentyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic AcidYield 103.3%

Procedure

In a manner similar to that of Example 1(a), by reaction of 2.36 g (5.8 mmol) of ethyl 3-[3-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]acrylate obtained in Example 13(f) with 1.6 g (6.3 mmol) of tert-butyl 6-bromohexanoate obtained above, 3.3 g (100%) of the expected compound were obtained in the form of a yellow oil.

Sources & evidence

ORD record
ord-ff0ed36521c64301b39625fb48968679
Source dataset
uspto-grants-2003_10
Patent number
US06632963B1

Reaction notes

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