Diisobutylaluminum hydride → (E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-en-1-ol

HRID 1883277Notes

Reaction equation

HRID 1883277 reaction equation
C([O:3][C:4](=O)[C:5]([F:27])=[C:6]([C:9]1[C:18]([O:19][CH2:20][O:21][CH3:22])=[CH:17][C:16]2[C:15]([CH3:24])([CH3:23])[CH2:14][CH2:13][C:12]([CH3:26])([CH3:25])[C:11]=2[CH:10]=1)[CH2:7][CH3:8])C.C(OC(=O)/C(/F)=C(\C1C(OCOC)=CC2C(C)(C)CCC(C)(C)C=2C=1)/CC)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[F:27]/[C:5](=[C:6](/[C:9]1[C:18]([O:19][CH2:20][O:21][CH3:22])=[CH:17][C:16]2[C:15]([CH3:24])([CH3:23])[CH2:14][CH2:13][C:12]([CH3:25])([CH3:26])[C:11]=2[CH:10]=1)\[CH2:7][CH3:8])/[CH2:4][OH:3]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 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 esterHCID 697259272-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enoic acid ethyl ester

Product 1

HCID 69729376(E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure C and using (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 (Intermediate 15, 3.3 g, 8.4 mmol), CH2Cl2 (50 mL), and DIBAL-H (33.6 mL, 1.0 M in THF, 33.6 mmol) followed by flash column chromatography on silica gel (10%→20% EtOAc-hexane), the title compound was obtained as a white solid (2.4 g, 75% over 2 steps).

Sources & evidence

ORD record
ord-3645678dc1ec44568d0403b4dcca922a
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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