115148-13-5

Basic information

• Product Name: (3aS,8bS)-7-Hydroxy-2-oxo-2,3,3a,8b-tetrahydro-benzo[b]furo[2,3-d]furan-8-carboxylic acid 2,2,2-trichloro-ethyl ester
• Synonyms: (3aS,8bS)-7-Hydroxy-2-oxo-2,3,3a,8b-tetrahydro-benzo[b]furo[2,3-d]furan-8-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS NO: 115148-13-5
• Molecular Weight: 367.57
• Mol File: 115148-13-5.mol

Chemical Properties

• CAS DataBase Reference: (3aS,8bS)-7-Hydroxy-2-oxo-2,3,3a,8b-tetrahydro-benzo[b]furo[2,3-d]furan-8-carboxylic acid 2,2,2-trichloro-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,8bS)-7-Hydroxy-2-oxo-2,3,3a,8b-tetrahydro-benzo[b]furo[2,3-d]furan-8-carboxylic acid 2,2,2-trichloro-ethyl ester(115148-13-5)
• EPA Substance Registry System: (3aS,8bS)-7-Hydroxy-2-oxo-2,3,3a,8b-tetrahydro-benzo[b]furo[2,3-d]furan-8-carboxylic acid 2,2,2-trichloro-ethyl ester(115148-13-5)

Safety Data

• Hazardous Substances Data: 115148-13-5(Hazardous Substances Data)

Upstream product

• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 115148-08-8 2,2,2-trichloroethyl 2,5-dioxo-2,5-dihydrobenzoat 

Relevant articles and documents

1,4-ADDITION OF 2-TRIMETHYLSILYLOXYFURAN TO QUINONES: A FACILE ROUTE TO THE FUROBENZOFURAN NUCLEUS

The uncatalysed addition of 2-trimethylsilyloxyfuran (3) to a range of activated quinones (4) and (6) yields the crystalline adducts (5) and (7) in 51-91percent yield.This novel furofuran-annulation to a quinone system provides a facile entry to the furobenzofuran ring system.

Synthesis of the cis-3a,8b-Dihydrofurobenzofuran-2(3H)-one Ring System via a Furofuran Annulation to Activated Benzoquinones

The uncatalysed addition of 2-(trimethylsiloxy)furan (4) to the 1,4-benzoquinones (5a-e) containing electron-withdrawing groups at C-2 gave the cis-3a,8b-dihydrofurobenzofuran-2(3H)-ones (6a-e) in 51-76percent yields.The 1,4-benzoquinones (5f, g, h) without electron-withdrawing groups at C-2 failed to undergo the furofuran annulation, with none of the desired adducts (6f, g, h) being isolated.The carboxylic acid adduct (6i; R=CO2H) was prepared indirectly by reductive hydrolysis of either the phenacyl adduct (6e) or the trichloroethyl ester adduct (6d) using zinc in acetic acid (9).Treatment of the methyl ketone adduct (6b) with acid effected a ring opening to the corresponding (benzofuran-2-yl)acetic acid.