Water → 2-[(1-Ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-3,3,3-trifluoro-1,2-propanediol

HRID 600749Notes

Reaction equation

[CH2:1]([C:3]1([CH2:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH2:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)[CH3:2].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:41]C)C=C4)N(CC2)C1.CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+].[OH2:142]>C(O)(C)(C)C>[CH2:1]([C:3]1([CH2:13][C:14]([OH:41])([C:16]([F:17])([F:18])[F:19])[CH2:15][OH:142])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

Conditions

Temperature: 30 °C

Procedure

1-Ethyl-1-[2-(trifluoromethyl)-2-propen-1-yl]-1,2,3,4-tetrahydronaphthalene (Intermediate 12) (100 mg, 0.373 mmole), AD-MIX-α (300 mg) and AD-MIX-β (300 mg) in t-butanol (2 ml) and water (2 ml) were stirred at room temperature. After 1 hour further AD-MIX-α (600 mg) and AD-MIX-β (600 mg) were added and the mixture was heated to 30° C. for 18 h. Sodium sulphite (2 g) was added together with water (5 ml) then stirred for 10 min. Extraction of the mixture with ethyl acetate (3×20 ml) followed by washing of the extract with 2M HCl (x2), 2M NaOH and evaporation of volatiles in vacuo gave a crude product. After purification (silica SPE, 85:15 cyclohexane:ethyl acetate) the title compound was obtained (30 mg, 27%).

Workup

extractionExtraction of the mixture with ethyl acetate (3×20 ml)
washby washing of the
extractionextract with 2M HCl (x2), 2M NaOH and evaporation of volatiles in vacuo

Sources & evidence

ORD record: ord-35d8bc4e2faa4608bc1aefd9ef7eebee
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902224B2

Reaction notes

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