6-Chloro-3-methylnaphthalen-1-ol → (S)-ethyl 2-tert-butoxy-2-(6-chloro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

HRID 926143Notes

Reaction equation

HRID 926143 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[C:20](C)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[Cl:32]C1C=C2C(=CC=1)C(O)=CC(C)=C2>>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:32])[CH:18]=2)[C:13]=1[O:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 896768476-Chloro-3-methylnaphthalen-1-olHCID 89681707(S)-ethyl 2-tert-butoxy-2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

Product 1

HCID 89681783(S)-ethyl 2-tert-butoxy-2-(6-chloro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

Procedure

(S)-ethyl 2-tert-butoxy-2-(6-chloro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate was prepared in a similar way as (S)-ethyl 2-tert-butoxy-2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate in Example 1 except using 6-chloro-3-methylnaphthalen-1-ol instead of 3,4-dimethylnaphthalen-1-ol. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=9.1 Hz, 1H), 7.78 (s, 1H), 7.58 (s, 1H), 7.51 (dd, J=9.0, 1.8 Hz, 1H), 5.70 (s, 1H), 4.17 (dqd, J=14.2, 7.1, 3.2 Hz, 2H), 2.55 (s, 3H), 1.20 (s, J=6.5 Hz, 9H), 1.17 (t, J=7.1 Hz, 3H).

Sources & evidence

ORD record
ord-373148f32b3d4ba485f010bf08316281
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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