Sodium borohydride → HCID 69057963, compound

HRID 2103026Notes

Reaction equation

HRID 2103026 reaction equation
[OH:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH:6]([CH3:17])[C:5]2=[O:18].ClC=C1C2(CCC2)OC2C(=C(C)C(O)=C(C)C=2C)C1=O.[BH4-].[Na+]>CO>[CH3:17][CH:6]1[C:7]2([CH2:10][CH2:9][CH2:8]2)[O:11][C:12]2[C:4](=[C:3]([CH3:19])[C:2]([OH:1])=[C:14]([CH3:15])[C:13]=2[CH3:16])[CH:5]1[OH:18]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11673337HCID 11673337, compoundHCID 69055162HCID 69055162, compound

Product 1

HCID 69057963HCID 69057963, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-hydroxy-3,5,7,8-tetramethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one, prepared by reduction of 3-(chloromethylene)-6-hydroxy-5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one (see Example 19) (168 mg) in 10 mL of MeOH was added NaBH4 (250 mg). The reaction mixture was allowed to stir at room temperature for 1 hour to give 3,5,7,8-tetramethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-4,6-diol. Subsequently 20 mL of MeOH was added to the reaction mixture, followed by 2 mL of conc. HCl. After 30 min, the reaction mixture was neutralized by adding saturated NaHCO3 and extracted with ethyl acetate. After drying it over anhydrous Na2SO4 and concentrating in vacuo, the residue was purified by flash chromatography eluted with 20% ethyl acetate in hexane to give 113.2 mg of 4-methoxy-3,5,7,8-tetramethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol as a yellow solid. 1H-NMR (300 MHz, CDCl3) δ=4.83 (s, 1H), 3.08 (s, 2H), 2.46 (s, 3H), 2.28 (s, 3H), 2.26 (s, 3H), 2.28-1.90 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=198.6, 149.9, 132.3, 131.8, 129.1, 128.8, 122.7, 57.9, 46.3, 35.1, 16.6, 15.7, 13.7, 13.3 ppm. MS: (m/z)=245.1 (M−OMe+).

Sources & evidence

ORD record
ord-b18cd94dc6ac42f69bcde11806ddb502
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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