Triethyl 2-fluoro-2-phosphonoacetate → (E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enoic acid ethyl ester

HRID 1883276Notes

Reaction equation

HRID 1883276 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].[Li]CCCC.[CH3:21][O:22][CH2:23][O:24][C:25]1[C:26]([C:39](=O)[CH2:40][CH3:41])=[CH:27][C:28]2[C:29]([CH3:38])([CH3:37])[CH2:30][CH2:31][C:32]([CH3:36])([CH3:35])[C:33]=2[CH:34]=1>C1COCC1>[CH2:2]([O:3][C:4](=[O:5])/[C:6](/[F:7])=[C:39](\[C:26]1[C:25]([O:24][CH2:23][O:22][CH3:21])=[CH:34][C:33]2[C:32]([CH3:36])([CH3:35])[CH2:31][CH2:30][C:29]([CH3:37])([CH3:38])[C:28]=2[CH:27]=1)/[CH2:40][CH3:41])[CH3:1]

Participants

5

Reactant 3

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 235108151-(3-Methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one2×HCID 178418339Butyllithium

Product 1

HCID 69725925(E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following General Procedure B and using triethyl 2-fluoro-2-phosphonoacetate (5.6 mL, 27.6 mmol), THF (50 mL), n-BuLi (17.3 mL, 1.6 M in hexane, 27.6 mmol), and 1-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one (Intermediate 14, 2.8 g, 9.2 mmol) in THF (10 mL), followed by flash column chromatography on silica gel (3% EtOAc-hexane), the title compound was obtained as a mixture containing minimal 2-Z isomer (3.3 g). The mixture was used directly in the next reaction.

Sources & evidence

ORD record
ord-5e2d59dd91e744f28bddb18f13b8ef3c
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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