Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate → HCID 59560467, compound

HRID 1177092Notes

Reaction equation

HRID 1177092 reaction equation
COC(C1C=C(OC2C=CC(S(C)(=O)=O)=CC=2)C=C2OC(C)CC=12)=O.[N:26]1([C:30]([C:32]2[CH:37]=[CH:36][C:35](F)=[C:34]([F:39])[CH:33]=2)=[O:31])[CH2:29][CH2:28][CH2:27]1.[CH3:40][O:41][C:42]([C:44]1[CH:54]=[C:53]([OH:55])[C:47]2[CH2:48][C:49]([CH3:52])([CH3:51])[O:50][C:46]=2[CH:45]=1)=[O:43]>>[CH3:40][O:41][C:42]([C:44]1[CH:54]=[C:53]([O:55][C:35]2[CH:36]=[CH:37][C:32]([C:30]([N:26]3[CH2:29][CH2:28][CH2:27]3)=[O:31])=[CH:33][C:34]=2[F:39])[C:47]2[CH2:48][C:49]([CH3:52])([CH3:51])[O:50][C:46]=2[CH:45]=1)=[O:43]

Participants

4

Reactant 3

HCID 25067323Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylateHCID 593468591-(3,4-Difluorobenzoyl)azetidineHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 59560467HCID 59560467, compound

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1f, from azetidin-1-yl-(3,4-difluoro-phenyl)-methanone (32a) (90 mg, 0.46 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) (117 mg, 0.53 mmol) to give a pale yellow oil (106 mg, 59% yield). 1H NMR (400 MHz, CDCl3) δ 7.51 (dd, J=10.86, 2.02 Hz, 1 H) 7.38-7.42 (m, 1 H) 7.21 (d, J=1.01 Hz, 1 H) 7.09 (d, J=1.01 Hz, 1 H) 6.99 (t, J=8.21 Hz, 1 H) 4.30-4.40 (m, 2 H) 4.20-4.29 (m, 2 H) 3.86 (s, 3 H) 2.97 (s, 2 H) 2.33-2.43 (m, 2 H) 1.50 (s, 6 H).

Sources & evidence

ORD record
ord-33e44840093c4799906e70c323f635b1
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

Loading…