Toluene → 2,3-Dihydro-3,3-dimethyl-5-hydroxy-2-piperidino-benzofuran

HRID 372408Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1(=[O:14])[CH:12]=[CH:11][C:10](=[O:13])[CH:9]=[CH:8]1.[C:15]1([CH3:21])[CH:20]=CC=C[CH:16]=1>>[CH3:16][C:15]1([CH3:21])[C:9]2[CH:8]=[C:7]([OH:14])[CH:12]=[CH:11][C:10]=2[O:13][CH:20]1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 1140Toluene

HCID 4650Quinone

HCID 8082Piperidine

Product 1

HCID 130848232,3-Dihydro-3,3-dimethyl-5-hydroxy-2-piperidino-benzofuran

Procedure

The process of Example 1 was repeated using 196.2 parts of piperidine in place of the morpholine. The product was the corresponding piperidino enamine which was reacted with benzoquinone in toluene to give 2,3-dihydro-3,3-dimethyl-5-hydroxy-2-piperidino-benzofuran. This was converted to 2,3-dihydro-3,3-dimethyl-2-piperidino-benzofuran-5-yl methanesulphonate and then to 2,3-dihydro-3,3-dimethyl-2-ethoxy-benzofuran-5-yl methane sulphonate as in Example 5.

Sources & evidence

ORD record: ord-cf5250d885204937873b7a769b29e7e2
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04091033

Reaction notes

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