Benzyl Alcohol → 6-Benzyloxy-1,3-benzoxathiol-2-one

HRID 732755Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:12]([O:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 6-hydroxy-1,3-benzoxathiol-2-one (16.8 g, 0.1 mol) in THF (1650 mL) and cool to 0° C. Sequentially add benzyl alcohol (16.2 g, 0.15 mol), triphenylphosphine (PPh3, 39.3 g, 0.15 mol), and diisopropylazodicarboxylate (30.3 g, 0.15 mol). Stir the reaction mixture at room temperature overnight. Add water (1500 mL) and extract the aqueous layer with EtOAc (3×1500 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 10-25% of EtOAc/hexane) to give 24.33 g of 6-benzyloxy-benzo[1,3]oxathiol-2-one (94%).

Workup

extractionAdd water (1500 mL) and extract the aqueous layer with EtOAc (3×1500 mL)
dry with materialCombine the organic layers and dry with Na2SO4
filtrationfilter
concentrationconcentrate
custompurify by flash column chromatography (silica gel, 10-25% of EtOAc/hexane)

Sources & evidence

ORD record: ord-2a4cda661eb5456cbd691e5996a7488a
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585977B2

Reaction notes

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