1,2-Naphthoquinone → HCID 57661929, compound

HRID 1665427Notes

Reaction equation

HRID 1665427 reaction equation
[SH:1][CH2:2][C:3]1([OH:9])[CH2:8][CH2:7][S:6][CH2:5][CH2:4]1.[C:10]1(=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]1=[O:20]>>[S:6]1[CH2:7][CH2:8][C:3]2([O:9][C:13]3[C:14]4[C:19]([C:10](=[O:21])[C:11](=[O:20])[C:12]=3[S:1][CH2:2]2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 106671,2-NaphthoquinoneHCID 86629712HCID 86629712, compound

Product 1

HCID 57661929HCID 57661929, compound

Procedure

The crude 4-(mercaptomethyl)tetrahydro-2H-thiopyran-4-ol was then reacted with naphthalene-1,2-dione as outlined in procedure F [both step (i) and (ii)] to afford crude 2′,3′,5′,6′-tetrahydrospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-thiopyran]-5,6-dione. The crude 2′,3′,5′,6′-tetrahydrospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-thiopyran]-5,6-dione was purified by flash column chromatography (SiO2, 25% EtOAc in hexanes) to afford the product as a purple solid. M.p.=221-223° C., 400 MHz 1H NMR (CDCl3) δ 8.05 (dd, d, J=7.4 Hz, 1.1 Hz, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.67 (dt, J=6.2 Hz, 1.1 Hz, 1H), 7.50 (dt, J=6.2 Hz, 1.1 Hz, 1H), 3.10-3.03 (m, 1H), 2.64-2.60 (m2, 2H), 2.47-2.43 (m, 2H), 1.99-1.92 (m, 2H); LCMS: 319 [M+H].

Workup

  1. customto afford crude 2′,3′,5′,6′-tetrahydrospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-thiopyran]-5,6-dione
  2. customThe crude 2′,3′,5′,6′-tetrahydrospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-thiopyran]-5,6-dione was purified by flash column chromatography (SiO2, 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9c9de54eb1c64c3e995c960f24ded5c4
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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