1,2-Naphthoquinone → HCID 57662035, compound

HRID 1665428Notes

Reaction equation

HRID 1665428 reaction equation
[SH:1][CH2:2][C:3]1([OH:15])[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[C:16]1(=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]1=[O:26]>>[C:9]1([CH:6]2[CH2:5][CH2:4][C:3]3([O:15][C:19]4[C:20]5[C:25]([C:16](=[O:27])[C:17](=[O:26])[C:18]=4[S:1][CH2:2]3)=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:8][CH2:7]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 106671,2-NaphthoquinoneHCID 86629713HCID 86629713, compound

Product 1

HCID 57662035HCID 57662035, compound

Procedure

The crude 1-(mercaptomethyl)-4-phenylcyclohexanol was then reacted with naphthalene-1,2-dione as outlined in procedure F [both step (i) and (ii)] to afford crude 4-phenylspiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione. The crude 4-phenylspiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione was purified by flash column chromatography (SiO2, 100% dichloromethane) to afford the product as a purple solid. M.p.=183-187° C.; 400 MHz 1H NMR (DMSO) δ: 7.92-7.78 (m, 3H), 7.60-7.56 (td, 1H), 7.34-7.18 (m, 5H), 3.09 (s, 2H), 2.71-2.66 (m, 1H), 2.20 (d, 2H), 1.90-1.72 (m, 6H); LCMS: 377 [M+H].

Workup

  1. customto afford crude 4-phenylspiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione
  2. customThe crude 4-phenylspiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione was purified by flash column chromatography (SiO2, 100% dichloromethane)

Sources & evidence

ORD record
ord-39a91f5f6136419980d581944e293704
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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