Water → HCID 14716854, compound

HRID 530541Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([O-])=[O:19])=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[K+]>C1COCC1>[CH:7]1([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:21][CH:22]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (2.0 M THF solution, 9.42 mL, 18.84 mmol) in dry THF (6.0 mL), 4-(cyclohexoxy)-benzoate (1.17 g, 4.71 mmol) in dry THF (30 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.70 mL), 3.0 M KOH solution (0.70 mL) and H2O (1.6 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness, affording the title compound (0.57 g, 59%), which was used in the next step without any further purification. 1H NMR (DMSO-d6): δ 1.21-1.47 (m, 5H), 1.49-1.57 (m, 1H), 1.64-1.77 (m, 2H), 1.87-1.95 (m, 2H), 4.25-4.33 (m, 1H), 4.40 (d, J=5.7 Hz, 2H), 5.00 (t, J=5.7 Hz, 1H), 6.87 (d, J=8.5 Hz, 2H), 7.19 (d, J=8.5 Hz, 2H).

Workup

additionwas added dropwise
waitThe mixture was left
customto react at rt for 4 h
customat 0° C
filtrationfiltered
customto remove the solid residue
dry with materialthe organic phase dried over Na2SO4
filtrationThe organic solution was again filtered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-85ae947199ac4d7e9c553f168a698823
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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