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Methyl chloroformate → (+/-)-Methyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamate

HRID 13942
Notes
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Reaction equation

HRID 13942 reaction equation
[Cl:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]2[O:6][CH:7]([CH2:9][NH2:10])[CH2:8][C:4]=2[CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:27]([O:29][CH3:30])=[O:28].CC1C=CC(S(OC)(=O)=O)=CC=1>>[Cl:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]2[O:6][CH:7]([CH2:9][NH:10][C:27](=[O:28])[O:29][CH3:30])[CH2:8][C:4]=2[CH:3]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6586Methyl chloroformateHCID 6645Methyl p-toluenesulfonateHCID 81531DiisopropylethylamineHCID 11436234(+/-)-(5-Chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylamine

Product 1

HCID 86598556(+/-)-Methyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamateYield 93%

Procedure

Treatment of (±)-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylamine (2.60 g, 9.62 mmol) with diisopropylethylamine (3.73 g, 28.85 mmol) and methyl chloroformate (1.36 g, 9.62 mmol) generally according to the procedure described for Intermediate 7 afforded 2.60 g (93%) of (±)-methyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamate as a white solid. mp 128-130° C.; Anal. calcd. for C15H14ClNO3: C, 61.76; H, 4.84; N, 4.80. Found: C, 61.43; H, 4.87; N, 4.68.

Sources & evidence

ORD record
ord-89a55ca56b2f4c6cad993fd79d796618
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728155B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes